N-aryltetrahydrophthalimide compounds

ABSTRACT

N-aryltetrahydrophthalimide compounds of the general formula I &lt;IMAGE&gt;  I  where n, R1, Y, R2 and R3 have the meanings stated in the claims and description, and a method for controlling undesirable plant growth.

This is a continuation of application Ser. No. 464,639, filed Jan. 5, 1990, U.S. Pat. No. 5,080,710 which is a continuation of Ser. No. 315,128, filed Feb. 24, 1989, now abandoned.

The present invention relates to N-phenyltetrahydrophthalimide compounds of the general formula I ##STR2## where the substituents and indices have the following meanings: n is 0 or 1, R¹ is hydrogen or halogen, Y is --O--, --S--, --CH₂ --, --S--CR⁴ R⁵ --, --O--CR⁴ R⁵ -- or --CH₂ --CR⁴ R⁵ --, R⁴ and R⁵ independently of one another being hydrogen or C₁ -C₃ -alkyl, R² is hydrogen or C₁ -C₃ -alkyl, R³ is a saturated or monounsaturated 5-membered or 6-membered ring which has an oxygen or sulfur atom in the ring and may be monosubstituted to trisubstituted by C₁ -C₃ -alkyl, or R³ is phenyl which is unsubstituted or monosubstituted to trisubstituted by C₁ - or C₂ -alkyl, halogen, methoxy, nitro and/or cyano, and, if n is 0 and Y is --CH₂ --, --CH₂ --CR⁴ R⁵ -- or --S--CR⁴ R⁵ --, R³ may furthermore be hydrogen, C₁ -C₅ -alkyl, C₃ - or C₄ -alkenyl, C₃ - or C₄ -alkynyl, C₁ -C₄ -haloalkyl, C₃ - or C₄ -haloalkenyl, C₁ - or C₂ -alkoxy-C₁ - or C₂ -alkyl or C₁ - or C₂ -alkoxy-C₁ -or C₂ -alkoxy-C₁ - or C₂ -alkyl or C₁ -C₆ -alkoxycarbonyl-substituted C₁ -C₃ -alkyl.

The present invention furthermore relates to a method for controlling undesirable plant growth and herbicides which contain these compounds.

N-aryl-substituted tetrahydrophthalimides having a herbicidal action are known. For example, EP-A-170 191 describes tetrahydrophthalimides, but their activity is unsatisfactory at low application rates.

It is an object of the present invention to provide appropriately improved tetrahydrophthalimide compounds.

We have found that this object is achieved in that the N-aryltetrahydrophthalimide compounds of the formula I which were defined at the outset have an advantageous herbicidal action, particularly by the postemergence method, and are selective with respect to a number of crops. Where these compounds are capable of forming stereoisomers, the invention relates to all isomers.

The compounds I are obtained, for example, by first reacting an appropriately substituted aniline of the formula II in a conventional manner in an inert organic solvent with an N-alkylating compound Z--(CHR²)_(n) R³ to give the aniline derivative III and then condensing this in an inert organic solvent with 3,4,5,6-tetrahydrophthalic anhydride to give the N-aryltetrahydrophthalimide I. ##STR3##

The radical Z in the alkylating reagent is a nucleophilic leaving group conventionally used in organic chemistry, such as halogen, e.g. chlorine, bromine or iodine, or sulfonyl, such as toluenesulfonyl or mesyl.

The alkylation is carried out in a conventional manner at up to 200° C., preferably from 0° to 150° C., in an aprotic polar solvent (e.g. acetone, acetonitrile or dimethylformamide), in the presence of a base (e.g. potassium carbonate, sodium hydroxide or sodium hydride).

The condensation of the aniline derivative III with 3,4,5,6-tetrahydrophthalic anhydride is carried out in a protic solvent, such as acetic acid, propionic acid or isobutyric acid, or in an aprotic solvent, such as toluene, xylene or dimethylformamide. The reaction is carried out, as a rule, at from 25° to 200° C., preferably from 70° to 140° C. When an aprotic solvent is used, it is advisable to remove the water continuously.

However, the compounds I are also obtained if an amine II is first condensed with 3,4,5,6-tetrahydrophthalic anhydride to give the N-phenyltetrahydrophthalimide IV, and the latter is then reacted with an N-alkylating compound Z--(CHR²)_(n) R³ to give I. ##STR4##

These reactions are carried out under conditions similar to those described above.

The required compounds II are prepared in a conventional manner: S. Gabriel et al., Chem. Ber. 12 (1879), 600; W. A. Sexton, J. Chem. Soc. 1939, 470; D. R. Shridar et al., Synthesis 1982, 986; Sandmeyer, Chem. Ber. 19 (1886), 2656, and D. R. Shridar et al., Indian. J. Chem. 24B (1985), 1263.

For the use of the compounds I in accordance with regulations, the following radicals are preferred substituents.

Halogen as used above is fluorine, chlorine or bromine, halogen radicals R¹ preferably being fluorine.

Alkyl includes branched and straight-chain radicals, e.g. methyl, ethyl, n-propyl and isopropyl.

The alkenyl and alknyl radicals may likewise be branched or straight-chain. Examples of alkenyl radicals in formula I are allyl, 2-propenyl, 2-butenyl, 3-butenyl and 2-isobutenyl, in particular allyl and 2-butenyl, and alkynyl radicals are, as a rule, propargyl, 2-butynyl or 3-butynyl.

The five-membered or six-membered heterocyclic ring of the formula I is preferably a hydrogenated or partially hydrogenated furan, thiophene, pyran or thiopyran ring.

Phenyl preferably includes the unsubstituted and monosubstituted derivatives, e.g. chlorophenyl, methylphenyl and methoxyphenyl.

The N-substituted tetrahydrophthalimides are obtainable from 3,4,5,6-tetrahydrophthalic anhydride and an appropriate aniline of the formula III, for example in a solvent at from 20° to 200° C., preferably from 40° to 150° C. Suitable solvents are, for example, lower alkanoic acids, such as glacial acetic acid or propionic acid, or aprotic solvents, such as toluene or xylene, in the presence of an acidic catalyst, for example an aromatic sulfonic acid.

Preferred compounds I are those in which R¹ is hydrogen or fluorine, R⁴ and R⁵ are each hydrogen or methyl, R² is hydrogen and R³ is 2- or 3-tetrahydrofuryl, 2- or 3-tetrahydrothienyl, 2-, 3- or 4-tetrahydropyranyl, 2-, 3- or 4-tetrahydrothiopyranyl, 5,6-dihydro-2H-pyranyl or 5,6-dihydro-2H-thiopyranyl.

Particularly active novel compounds are listed in Tables I, II, IIa, III, IIIa, IV, IVa, V and VI below.

                  TABLE I                                                          ______________________________________                                          ##STR5##                                                                      R.sup.1 R.sup.2  R.sup.3        R.sup.4                                                                               R.sup.5                                 ______________________________________                                         H       H                                                                                        ##STR6##      H      H                                       F       H                                                                                        ##STR7##      H      H                                       H       CH.sub.3                                                                                 ##STR8##      H      H                                       F       CH.sub.3                                                                                 ##STR9##      H      H                                       H       H                                                                                        ##STR10##     H      H                                       F       H                                                                                        ##STR11##     H      H                                       H       CH.sub.3                                                                                 ##STR12##     H      H                                       F       CH.sub.3                                                                                 ##STR13##     H      H                                       H       H                                                                                        ##STR14##     H      H                                       F       H                                                                                        ##STR15##     H      H                                       H       CH.sub.3                                                                                 ##STR16##     H      H                                       F       CH.sub.3                                                                                 ##STR17##     H      H                                       H       H                                                                                        ##STR18##     H      H                                       F       H                                                                                        ##STR19##     H      H                                       H       CH.sub.3                                                                                 ##STR20##     H      H                                       F       CH.sub.3                                                                                 ##STR21##     H      H                                       H       H                                                                                        ##STR22##     H      H                                       F       H                                                                                        ##STR23##     H      H                                       H       CH.sub.3                                                                                 ##STR24##     H      H                                       F       CH.sub.3                                                                                 ##STR25##     H      H                                       H       H                                                                                        ##STR26##     CH.sub.3                                                                              H                                       F       H                                                                                        ##STR27##     CH.sub.3                                                                              H                                       H       CH.sub.3                                                                                 ##STR28##     CH.sub.3                                                                              H                                       F       CH.sub.3                                                                                 ##STR29##     CH.sub.3                                                                              H                                       H       H                                                                                        ##STR30##     CH.sub.3                                                                              CH.sub.3                                F       H                                                                                        ##STR31##     CH.sub.3                                                                              CH.sub.3                                H       CH.sub.3                                                                                 ##STR32##     CH.sub.3                                                                              CH.sub.3                                F       CH.sub.3                                                                                 ##STR33##     CH.sub.3                                                                              CH.sub.3                                H       H                                                                                        ##STR34##     H      H                                       F       H                                                                                        ##STR35##     H      H                                       H       CH.sub.3                                                                                 ##STR36##     H      H                                       F       CH.sub.3                                                                                 ##STR37##     H      H                                       H       H                                                                                        ##STR38##     CH.sub.3                                                                              H                                       F       H                                                                                        ##STR39##     CH.sub.3                                                                              H                                       H       CH.sub.3                                                                                 ##STR40##     CH.sub.3                                                                              H                                       F       CH.sub.3                                                                                 ##STR41##     CH.sub.3                                                                              H                                       H       H                                                                                        ##STR42##     CH.sub.3                                                                              CH.sub.3                                F       H                                                                                        ##STR43##     CH.sub.3                                                                              CH.sub.3                                H       CH.sub.3                                                                                 ##STR44##     CH.sub.3                                                                              CH.sub.3                                F       CH.sub.3                                                                                 ##STR45##     CH.sub.3                                                                              CH.sub.3                                H       H                                                                                        ##STR46##     H      H                                       F       H                                                                                        ##STR47##     H      H                                       H       CH.sub.3                                                                                 ##STR48##     H      H                                       F       CH.sub.3                                                                                 ##STR49##     H      H                                       H       H                                                                                        ##STR50##     CH.sub.3                                                                              H                                       F       H                                                                                        ##STR51##     CH.sub.3                                                                              H                                       H       CH.sub.3                                                                                 ##STR52##     CH.sub.3                                                                              H                                       F       CH.sub. 3                                                                                ##STR53##     CH.sub.3                                                                              H                                       H       H                                                                                        ##STR54##     H      H                                       F       H                                                                                        ##STR55##     H      H                                       H       CH.sub.3                                                                                 ##STR56##     H      H                                       F       CH.sub.3                                                                                 ##STR57##     H      H                                       H       H                                                                                        ##STR58##     CH.sub.3                                                                              H                                       F       H                                                                                        ##STR59##     CH.sub.3                                                                              H                                       H       CH.sub.3                                                                                 ##STR60##     CH.sub.3                                                                              H                                       F       CH.sub.3                                                                                 ##STR61##     CH.sub.3                                                                              H                                       H       H                                                                                        ##STR62##     CH.sub.3                                                                              CH.sub.3                                F       H                                                                                        ##STR63##     CH.sub.3                                                                              CH.sub.3                                H       CH.sub.3                                                                                 ##STR64##     CH.sub.3                                                                              CH.sub.3                                F       CH.sub.3                                                                                 ##STR65##     CH.sub.3                                                                              CH.sub.3                                H       H                                                                                        ##STR66##     H      H                                       F       H                                                                                        ##STR67##     H      H                                       H       CH.sub.3                                                                                 ##STR68##     H      H                                       F       CH.sub.3                                                                                 ##STR69##     H      H                                       H       H                                                                                        ##STR70##     CH.sub.3                                                                              H                                       F       H                                                                                        ##STR71##     CH.sub.3                                                                              H                                       H       CH.sub.3                                                                                 ##STR72##     CH.sub.3                                                                              H                                       F       CH.sub.3                                                                                 ##STR73##     CH.sub.3                                                                              H                                       H       H                                                                                        ##STR74##     CH.sub.3                                                                              CH.sub.3                                F       H                                                                                        ##STR75##     CH.sub.3                                                                              CH.sub.3                                H       CH.sub.3                                                                                 ##STR76##     CH.sub.3                                                                              CH.sub.3                                F       CH.sub.3                                                                                 ##STR77##     CH.sub.3                                                                              CH.sub.3                                H       H                                                                                        ##STR78##     CH.sub.3                                                                              CH.sub.3                                F       H                                                                                        ##STR79##     CH.sub.3                                                                              CH.sub.3                                H       CH.sub.3                                                                                 ##STR80##     CH.sub.3                                                                              CH.sub.3                                F       CH.sub.3                                                                                 ##STR81##     CH.sub.3                                                                              CH.sub.3                                H       H                                                                                        ##STR82##     H      H                                       F       H                                                                                        ##STR83##     H      H                                       H       CH.sub.3                                                                                 ##STR84##     H      H                                       F       CH.sub.3                                                                                 ##STR85##     H      H                                       H       H                                                                                        ##STR86##     CH.sub.3                                                                              H                                       F       H                                                                                        ##STR87##     CH.sub.3                                                                              H                                       H       CH.sub.3                                                                                 ##STR88##     CH.sub.3                                                                              H                                       F       CH.sub.3                                                                                 ##STR89##     CH.sub.3                                                                              H                                       H       H                                                                                        ##STR90##     CH.sub.3                                                                              CH.sub.3                                F       H                                                                                        ##STR91##     CH.sub.3                                                                              CH.sub.3                                H       CH.sub.3                                                                                 ##STR92##     CH.sub.3                                                                              CH.sub.3                                F       CH.sub.3                                                                                 ##STR93##     CH.sub.3                                                                              CH.sub.3                                H       H                                                                                        ##STR94##     H      H                                       F       H                                                                                        ##STR95##     H      H                                       H       CH.sub.3                                                                                 ##STR96##     H      H                                       F       CH.sub.3                                                                                 ##STR97##     H      H                                       H       H                                                                                        ##STR98##     CH.sub.3                                                                              H                                       F       H                                                                                        ##STR99##     CH.sub.3                                                                              H                                       H       CH.sub.3                                                                                 ##STR100##    CH.sub.3                                                                              H                                       F       CH.sub.3                                                                                 ##STR101##    CH.sub.3                                                                              H                                       H       H                                                                                        ##STR102##    H      H                                       F       H                                                                                        ##STR103##    H      H                                       H       CH.sub.3                                                                                 ##STR104##    H      H                                       F       CH.sub.3                                                                                 ##STR105##    H      H                                       H       H                                                                                        ##STR106##    H      H                                       F       H                                                                                        ##STR107##    H      H                                       H       CH.sub.3                                                                                 ##STR108##    H      H                                       F       CH.sub.3                                                                                 ##STR109##    H      H                                       H       H                                                                                        ##STR110##    H      H                                       F       H                                                                                        ##STR111##    H      H                                       H       CH.sub.3                                                                                 ##STR112##    H      H                                       F       CH.sub.3                                                                                 ##STR113##    H      H                                       H       H                                                                                        ##STR114##    H      H                                       F       H                                                                                        ##STR115##    H      H                                       H       CH.sub.3                                                                                 ##STR116##    H      H                                       F       CH.sub.3                                                                                 ##STR117##    H      H                                       H       H                                                                                        ##STR118##    H      H                                       F       H                                                                                        ##STR119##    H      H                                       H       CH.sub.3                                                                                 ##STR120##    H      H                                       F       CH.sub.3                                                                                 ##STR121##    H      H                                       H       H                                                                                        ##STR122##    CH.sub.3                                                                              H                                       F       H                                                                                        ##STR123##    CH.sub.3                                                                              H                                       H       CH.sub.3                                                                                 ##STR124##    CH.sub.3                                                                              H                                       F       CH.sub.3                                                                                 ##STR125##    CH.sub.3                                                                              H                                       H       H                                                                                        ##STR126##    CH.sub.3                                                                              CH.sub.3                                F       H                                                                                        ##STR127##    CH.sub.3                                                                              CH.sub.3                                H       CH.sub.3                                                                                 ##STR128##    CH.sub.3                                                                              CH.sub.3                                F       CH.sub.3                                                                                 ##STR129##    CH.sub.3                                                                              CH.sub.3                                H       H                                                                                        ##STR130##    H      H                                       F       H                                                                                        ##STR131##    H      H                                       H       CH.sub.3                                                                                 ##STR132##    H      H                                       F       CH.sub.3                                                                                 ##STR133##    H      H                                       H       H                                                                                        ##STR134##    CH.sub.3                                                                              H                                       F       H                                                                                        ##STR135##    CH.sub.3                                                                              H                                       H       CH.sub.3                                                                                 ##STR136##    CH.sub.3                                                                              H                                       F       CH.sub.3                                                                                 ##STR137##    CH.sub.3                                                                              H                                       H       H                                                                                        ##STR138##    CH.sub.3                                                                              CH.sub.3                                F       H                                                                                        ##STR139##    CH.sub.3                                                                              CH.sub.3                                H       CH.sub.3                                                                                 ##STR140##    CH.sub.3                                                                              CH.sub.3                                F       CH.sub.3                                                                                 ##STR141##    CH.sub.3                                                                              CH.sub.3                                H       H                                                                                        ##STR142##    H      H                                       F       H                                                                                        ##STR143##    H      H                                       H       CH.sub.3                                                                                 ##STR144##    H      H                                       F       CH.sub.3                                                                                 ##STR145##    H      H                                       H       H                                                                                        ##STR146##    CH.sub.3                                                                              H                                       F       H                                                                                        ##STR147##    CH.sub.3                                                                              H                                       H       CH.sub.3                                                                                 ##STR148##    CH.sub.3                                                                              H                                       F       CH.sub.3                                                                                 ##STR149##    CH.sub.3                                                                              H                                       H       H                                                                                        ##STR150##    H      H                                       F       H                                                                                        ##STR151##    H      H                                       H       CH.sub.3                                                                                 ##STR152##    H      H                                       F       CH.sub.3                                                                                 ##STR153##    H      H                                       H       H                                                                                        ##STR154##    CH.sub.3                                                                              H                                       F       H                                                                                        ##STR155##    CH.sub.3                                                                              H                                       H       CH.sub.3                                                                                 ##STR156##    CH.sub.3                                                                              H                                       F       CH.sub.3                                                                                 ##STR157##    CH.sub.3                                                                              H                                       H       H                                                                                        ##STR158##    CH.sub.3                                                                              CH.sub.3                                F       H                                                                                        ##STR159##    CH.sub.3                                                                              CH.sub.3                                H       CH.sub.3                                                                                 ##STR160##    CH.sub.3                                                                              CH.sub.3                                F       CH.sub.3                                                                                 ##STR161##    CH.sub.3                                                                              CH.sub.3                                H       H                                                                                        ##STR162##    H      H                                       F       H                                                                                        ##STR163##    H      H                                       H       CH.sub.3                                                                                 ##STR164##    H      H                                       F       CH.sub.3                                                                                 ##STR165##    H      H                                       H       H                                                                                        ##STR166##    CH.sub.3                                                                              H                                       F       H                                                                                        ##STR167##    CH.sub.3                                                                              H                                       H       CH.sub.3                                                                                 ##STR168##    CH.sub.3                                                                              H                                       F       CH.sub.3                                                                                 ##STR169##    CH.sub.3                                                                              H                                       H       H                                                                                        ##STR170##    CH.sub.3                                                                              CH.sub.3                                F       H                                                                                        ##STR171##    CH.sub.3                                                                              CH.sub.3                                H       CH.sub.3                                                                                 ##STR172##    CH.sub.3                                                                              CH.sub.3                                F       CH.sub.3                                                                                 ##STR173##    CH.sub.3                                                                              CH.sub.3                                H       H                                                                                        ##STR174##    CH.sub.3                                                                              CH.sub.3                                F       H                                                                                        ##STR175##    CH.sub.3                                                                              CH.sub.3                                H       CH.sub.3                                                                                 ##STR176##    CH.sub.3                                                                              CH.sub.3                                F       CH.sub.3                                                                                 ##STR177##    CH.sub.3                                                                              CH.sub.3                                H       H                                                                                        ##STR178##    H      H                                       F       H                                                                                        ##STR179##    H      H                                       H       CH.sub.3                                                                                 ##STR180##    H      H                                       F       CH.sub.3                                                                                 ##STR181##    H      H                                       H       H                                                                                        ##STR182##    CH.sub.3                                                                              H                                       F       H                                                                                        ##STR183##    CH.sub.3                                                                              H                                       H       CH.sub.3                                                                                 ##STR184##    CH.sub.3                                                                              H                                       F       CH.sub.3                                                                                 ##STR185##    CH.sub.3                                                                              H                                       H       H                                                                                        ##STR186##    CH.sub.3                                                                              CH.sub.3                                F       H                                                                                        ##STR187##    CH.sub.3                                                                              CH.sub.3                                H       CH.sub.3                                                                                 ##STR188##    CH.sub.3                                                                              CH.sub.3                                F       CH.sub.3                                                                                 ##STR189##    CH.sub.3                                                                              CH.sub.3                                H       H                                                                                        ##STR190##    H      H                                       F       H                                                                                        ##STR191##    H      H                                       H       CH.sub.3                                                                                 ##STR192##    H      H                                       F       CH.sub.3                                                                                 ##STR193##    H      H                                       H       H                                                                                        ##STR194##    CH.sub.3                                                                              H                                       F       H                                                                                        ##STR195##    CH.sub.3                                                                              H                                       H       CH.sub.3                                                                                 ##STR196##    CH.sub.3                                                                              H                                       F       CH.sub.3                                                                                 ##STR197##    CH.sub.3                                                                              H                                       H       H                                                                                        ##STR198##    H      H                                       F       H                                                                                        ##STR199##    H      H                                       H       CH.sub.3                                                                                 ##STR200##    H      H                                       F       CH.sub.3                                                                                 ##STR201##    H      H                                       H       H                                                                                        ##STR202##    CH.sub.3                                                                              H                                       F       H                                                                                        ##STR203##    CH.sub.3                                                                              H                                       H       CH.sub.3                                                                                 ##STR204##    CH.sub.3                                                                              H                                       F       CH.sub.3                                                                                 ##STR205##    CH.sub.3                                                                              H                                       H       H                                                                                        ##STR206##    CH.sub.3                                                                              CH.sub.3                                F       H                                                                                        ##STR207##    CH.sub.3                                                                              CH.sub.3                                H       CH.sub.3                                                                                 ##STR208##    CH.sub.3                                                                              CH.sub.3                                F       CH.sub.3                                                                                 ##STR209##    CH.sub.3                                                                              CH.sub.3                                H       H                                                                                        ##STR210##    H      H                                       F       H                                                                                        ##STR211##    H      H                                       H       CH.sub.3                                                                                 ##STR212##    H      H                                       F       CH.sub.3                                                                                 ##STR213##    H      H                                       H       H                                                                                        ##STR214##    H      H                                       F       H                                                                                        ##STR215##    H      H                                       H       CH.sub.3                                                                                 ##STR216##    H      H                                       F       CH.sub.3                                                                                 ##STR217##    H      H                                       H       H                                                                                        ##STR218##    H      H                                       F       H                                                                                        ##STR219##    H      H                                       H       CH.sub.3                                                                                 ##STR220##    H      H                                       F       CH.sub.3                                                                                 ##STR221##    H      H                                       ______________________________________                                    

                  TABLE II                                                         ______________________________________                                          ##STR222##                                                                    R.sup.1 R.sup.2  R.sup.3       R.sup.4                                                                               R.sup.5                                  ______________________________________                                         H       H                                                                                        ##STR223##   H      H                                        F       H                                                                                        ##STR224##   H      H                                        H       CH.sub.3                                                                                 ##STR225##   H      H                                        F       CH.sub.3                                                                                 ##STR226##   H      H                                        H       H                                                                                        ##STR227##   H      H                                        F       H                                                                                        ##STR228##   H      H                                        H       CH.sub.3                                                                                 ##STR229##   H      H                                        F       CH.sub.3                                                                                 ##STR230##   H      H                                        H       H                                                                                        ##STR231##   H      H                                        F       H                                                                                        ##STR232##   H      H                                        H       CH.sub.3                                                                                 ##STR233##   H      H                                        F       CH.sub.3                                                                                 ##STR234##   H      H                                        H       H                                                                                        ##STR235##   H      H                                        F       H                                                                                        ##STR236##   H      H                                        H       CH.sub.3                                                                                 ##STR237##   H      H                                        F       CH.sub.3                                                                                 ##STR238##   H      H                                        H       H                                                                                        ##STR239##   H      H                                        F       H                                                                                        ##STR240##   H      H                                        H       CH.sub.3                                                                                 ##STR241##   H      H                                        F       CH.sub.3                                                                                 ##STR242##   H      H                                        H       H                                                                                        ##STR243##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR244##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR245##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR246##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR247##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR248##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR249##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR250##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR251##   H      H                                        F       H                                                                                        ##STR252##   H      H                                        H       CH.sub.3                                                                                 ##STR253##   H      H                                        F       CH.sub.3                                                                                 ##STR254##   H      H                                        H       H                                                                                        ##STR255##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR256##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR257##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR258##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR259##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR260##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR261##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR262##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR263##   H      H                                        F       H                                                                                        ##STR264##   H      H                                        H       CH.sub.3                                                                                 ##STR265##   H      H                                        F       CH.sub.3                                                                                 ##STR266##   H      H                                        H       H                                                                                        ##STR267##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR268##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR269##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR270##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR271##   H      H                                        F       H                                                                                        ##STR272##   H      H                                        H       CH.sub.3                                                                                 ##STR273##   H      H                                        F       CH.sub.3                                                                                 ##STR274##   H      H                                        H       H                                                                                        ##STR275##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR276##   CH.sub.3                                                                              H                                        H       CH.sub. 3                                                                                ##STR277##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR278##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR279##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR280##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR281##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR282##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR283##   H      H                                        F       H                                                                                        ##STR284##   H      H                                        H       CH.sub.3                                                                                 ##STR285##   H      H                                        F       CH.sub.3                                                                                 ##STR286##   H      H                                        H       H                                                                                        ##STR287##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR288##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR289##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR290##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR291##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR292##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR293##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR294##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR295##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR296##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR297##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR298##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR299##   H      H                                        F       H                                                                                        ##STR300##   H      H                                        H       CH.sub.3                                                                                 ##STR301##   H      H                                        F       CH.sub.3                                                                                 ##STR302##   H      H                                        H       H                                                                                        ##STR303##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR304##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR305##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR306##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR307##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR308##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR309##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR310##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR311##   H      H                                        F       H                                                                                        ##STR312##   H      H                                        H       CH.sub.3                                                                                 ##STR313##   H      H                                        F       CH.sub.3                                                                                 ##STR314##   H      H                                        H       H                                                                                        ##STR315##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR316##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR317##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR318##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR319##   H      H                                        F       H                                                                                        ##STR320##   H      H                                        H       CH.sub.3                                                                                 ##STR321##   H      H                                        F       CH.sub.3                                                                                 ##STR322##   H      H                                        H       H                                                                                        ##STR323##   H      H                                        F       H                                                                                        ##STR324##   H      H                                        H       CH.sub.3                                                                                 ##STR325##   H      H                                        F       CH.sub.3                                                                                 ##STR326##   H      H                                        H       H                                                                                        ##STR327##   H      H                                        F       H                                                                                        ##STR328##   H      H                                        H       CH.sub.3                                                                                 ##STR329##   H      H                                        F       CH.sub.3                                                                                 ##STR330##   H      H                                        H       H                                                                                        ##STR331##   H      H                                        F       H                                                                                        ##STR332##   H      H                                        H       CH.sub.3                                                                                 ##STR333##   H      H                                        F       CH.sub.3                                                                                 ##STR334##   H      H                                        H       H                                                                                        ##STR335##   H      H                                        F       H                                                                                        ##STR336##   H      H                                        H       CH.sub.3                                                                                 ##STR337##   H      H                                        F       CH.sub.3                                                                                 ##STR338##   H      H                                        H       H                                                                                        ##STR339##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR340##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR341##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR342##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR343##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR344##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR345##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR346##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR347##   H      H                                        F       H                                                                                        ##STR348##   H      H                                        H       CH.sub. 3                                                                                ##STR349##   H      H                                        F       CH.sub.3                                                                                 ##STR350##   H      H                                        H       H                                                                                        ##STR351##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR352##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR353##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR354##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR355##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR356##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR357##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR358##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR359##   H      H                                        F       H                                                                                        ##STR360##   H      H                                        H       CH.sub. 3                                                                                ##STR361##   H      H                                        F       CH.sub.3                                                                                 ##STR362##   H      H                                        H       H                                                                                        ##STR363##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR364##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR365##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR366##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR367##   H      H                                        F       H                                                                                        ##STR368##   H      H                                        H       CH.sub.3                                                                                 ##STR369##   H      H                                        F       CH.sub.3                                                                                 ##STR370##   H      H                                        H       H                                                                                        ##STR371##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR372##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR373##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR374##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR375##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR376##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR377##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR378##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR379##   H      H                                        F       H                                                                                        ##STR380##   H      H                                        H       CH.sub.3                                                                                 ##STR381##   H      H                                        F       CH.sub.3                                                                                 ##STR382##   H      H                                        H       H                                                                                        ##STR383##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR384##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR385##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR386##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR387##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR388##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR389##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR390##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR391##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR392##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR393##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR394##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR395##   H      H                                        F       H                                                                                        ##STR396##   H      H                                        H       CH.sub.3                                                                                 ##STR397##   H      H                                        F       CH.sub.3                                                                                 ##STR398##   H      H                                        H       H                                                                                        ##STR399##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR400##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR401##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR402##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR403##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR404##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR405##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR406##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR407##   H      H                                        F       H                                                                                        ##STR408##   H      H                                        H       CH.sub.3                                                                                 ##STR409##   H      H                                        F       CH.sub.3                                                                                 ##STR410##   H      H                                        H       H                                                                                        ##STR411##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR412##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR413##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR414##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR415##   H      H                                        F       H                                                                                        ##STR416##   H      H                                        H       CH.sub.3                                                                                 ##STR417##   H      H                                        F       CH.sub.3                                                                                 ##STR418##   H      H                                        H       H                                                                                        ##STR419##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR420##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR421##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR422##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR423##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR424##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR425##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR426##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR427##   H      H                                        F       H                                                                                        ##STR428##   H      H                                        H       CH.sub.3                                                                                 ##STR429##   H      H                                        F       CH.sub.3                                                                                 ##STR430##   H      H                                        H       H                                                                                        ##STR431##   H      H                                        F       H                                                                                        ##STR432##   H      H                                        H       CH.sub.3                                                                                 ##STR433##   H      H                                        F       CH.sub.3                                                                                 ##STR434##   H      H                                        H       H                                                                                        ##STR435##   H      H                                        F       H                                                                                        ##STR436##   H      H                                        H       CH.sub.3                                                                                 ##STR437##   H      H                                        F       CH.sub.3                                                                                 ##STR438##   H      H                                        ______________________________________                                    

                  TABLE IIa                                                        ______________________________________                                          ##STR439##                                                                    R.sup.1  R.sup.4  R.sup.5  A                                                   ______________________________________                                         H        H        H        H                                                   F        H        H        H                                                   H        CH.sub.3 H        H                                                   F        CH.sub.3 H        H                                                   H        H        H        CH.sub.3                                            F        H        H        CH.sub.3                                            H        CH.sub.3 H        CH.sub.3                                            F        CH.sub.3 H        CH.sub.3                                            H        H        H        CH.sub.2 CH.sub.3                                   F        H        H        CH.sub.2 CH.sub.3                                   H        CH.sub.3 H        CH.sub.2 CH.sub.3                                   F        CH.sub.3 H        CH.sub.2 CH.sub.3                                   H        H        H        CH(CH.sub.3).sub.2                                  F        H        H        CH(CH.sub.3).sub.2                                  H        CH.sub.3 H        CH(CH.sub.3).sub.2                                  F        CH.sub.3 H        CH(CH.sub.3).sub.2                                  H        H        H        CH.sub.2 CHCH.sub.2                                 F        H        H        CH.sub.2 CHCH.sub.2                                 H        CH.sub.3 H        CH.sub.2 CHCH.sub.2                                 F        CH.sub.3 H        CH.sub.2 CHCH.sub.2                                 H        H        H        CH.sub.2 CHCHCH.sub.3                               F        H        H        CH.sub.2 CHCHCH.sub.3                               H        CH.sub.3 H        CH.sub.2 CHCHCH.sub.3                               F        CH.sub.3 H        CH.sub.2 CHCHCH.sub.3                               H        H        H        CH.sub.2 CCH                                        F        H        H        CH.sub.2 CCH                                        H        CH.sub.3 H        CH.sub.2 CCH                                        F        CH.sub.3 H        CH.sub.2 CCH                                        H        H        H        CH.sub.2 CCCH.sub.3                                 F        H        H        CH.sub.2 CCCH.sub.3                                 H        CH.sub.3 H        CH.sub.2 CCCH.sub.3                                 F        CH.sub.3 H        CH.sub.2 CCCH.sub.3                                 H        H        H        CH.sub.2 OCH.sub.3                                  F        H        H        CH.sub.2 OCH.sub. 3                                 H        CH.sub.3 H        CH.sub.2 OCH.sub.3                                  F        CH.sub.3 H        CH.sub.2 OCH.sub.3                                  H        H        H        (CH.sub.2).sub.2 OCH.sub.3                          F        H        H        (CH.sub.2).sub.2 OCH.sub.3                          H        CH.sub.3 H        (CH.sub.2).sub.2 OCH.sub.3                          F        CH.sub.3 H        (CH.sub.2).sub.2 OCH.sub.3                          H        H        H        CH.sub.2 CO.sub.2 CH.sub.3                          F        H        H        CH.sub.2 CO.sub.2 CH.sub.3                          H        CH.sub.3 H        CH.sub.2 CO.sub.2 CH.sub.3                          F        CH.sub.3 H        CH.sub.2 CO.sub.2 CH.sub.3                          H        H        H        CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                 F        H        H        CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                 H        CH.sub.3 H        CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                 F        CH.sub.3 H        CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                 H        H        H        CH(CH.sub.3)CO.sub.2 CH.sub.3                       F        H        H        CH(CH.sub.3)CO.sub.2 CH.sub.3                       H        CH.sub.3 H        CH(CH.sub.3)CO.sub.2 CH.sub.3                       F        CH.sub.3 H        CH(CH.sub.3)CO.sub.2 CH.sub.3                       H        H        H        CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3              F        H        H        CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3              H        CH.sub.3 H        CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3              F        CH.sub.3 H        CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3              H        CH.sub.3 CH.sub.3 H                                                   F        CH.sub.3 CH.sub.3 H                                                   H        CH.sub.3 CH.sub.3 CH.sub.3                                            F        CH.sub.3 CH.sub.3 CH.sub.3                                            H        CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.3                                   F        CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.3                                   H        CH.sub.3 CH.sub.3 CH.sub.2 CHCH.sub.2                                 F        CH.sub.3 CH.sub.3 CH.sub.2 CHCH.sub.2                                 H        CH.sub.3 CH.sub.3 CH.sub.2 CCH                                        F        CH.sub.3 CH.sub.3 CH.sub.2 CCH                                        H        CH.sub.3 CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3                          F        CH.sub.3 CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3                          H        CH.sub.3 CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3                          F        CH.sub.3 CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3                          H        CH.sub.3 CH.sub.3 CH(CH.sub.3)CO.sub.2 CH.sub.3                       F        CH.sub.3 CH.sub.3 CH(CH.sub.3)CO.sub.2 CH.sub.3                       ______________________________________                                    

                  TABLE III                                                        ______________________________________                                          ##STR440##                                                                    R.sup.1 R.sup.2  R.sup.3       R.sup.4                                                                               R.sup.5                                  ______________________________________                                         H       H                                                                                        ##STR441##   H      H                                        F       H                                                                                        ##STR442##   H      H                                        H       CH.sub.3                                                                                 ##STR443##   H      H                                        F       CH.sub.3                                                                                 ##STR444##   H      H                                        H       H                                                                                        ##STR445##   H      H                                        F       H                                                                                        ##STR446##   H      H                                        H       CH.sub.3                                                                                 ##STR447##   H      H                                        F       CH.sub.3                                                                                 ##STR448##   H      H                                        H       H                                                                                        ##STR449##   H      H                                        F       H                                                                                        ##STR450##   H      H                                        H       CH.sub.3                                                                                 ##STR451##   H      H                                        F       CH.sub.3                                                                                 ##STR452##   H      H                                        H       H                                                                                        ##STR453##   H      H                                        F       H                                                                                        ##STR454##   H      H                                        H       CH.sub.3                                                                                 ##STR455##   H      H                                        F       CH.sub.3                                                                                 ##STR456##   H      H                                        H       H                                                                                        ##STR457##   H      H                                        F       H                                                                                        ##STR458##   H      H                                        H       CH.sub.3                                                                                 ##STR459##   H      H                                        F       CH.sub.3                                                                                 ##STR460##   H      H                                        H       H                                                                                        ##STR461##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR462##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR463##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR464##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR465##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR466##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR467##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR468##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR469##   H      H                                        F       H                                                                                        ##STR470##   H      H                                        H       CH.sub.3                                                                                 ##STR471##   H      H                                        F       CH.sub.3                                                                                 ##STR472##   H      H                                        H       H                                                                                        ##STR473##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR474##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR475##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR476##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR477##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR478##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR479##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR480##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR481##   H      H                                        F       H                                                                                        ##STR482##   H      H                                        H       CH.sub.3                                                                                 ##STR483##   H      H                                        F       CH.sub.3                                                                                 ##STR484##   H      H                                        H       H                                                                                        ##STR485##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR486##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR487##   CH.sub.3                                                                              H                                        F       CH.sub. 3                                                                                ##STR488##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR489##   H      H                                        F       H                                                                                        ##STR490##   H      H                                        H       CH.sub.3                                                                                 ##STR491##   H      H                                        F       CH.sub.3                                                                                 ##STR492##   H      H                                        H       H                                                                                        ##STR493##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR494##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR495##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR496##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR497##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR498##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR499##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR500##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR501##   H      H                                        F       H                                                                                        ##STR502##   H      H                                        H       CH.sub.3                                                                                 ##STR503##   H      H                                        F       CH.sub.3                                                                                 ##STR504##   H      H                                        H       H                                                                                        ##STR505##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR506##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR507##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR508##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR509##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR510##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR511##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR512##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR513##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR514##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR515##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR516##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR517##   H      H                                        F       H                                                                                        ##STR518##   H      H                                        H       CH.sub.3                                                                                 ##STR519##   H      H                                        F       CH.sub.3                                                                                 ##STR520##   H      H                                        H       H                                                                                        ##STR521##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR522##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR523##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR524##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR525##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR526##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR527##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR528##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR529##   H      H                                        F       H                                                                                        ##STR530##   H      H                                        H       CH.sub.3                                                                                 ##STR531##   H      H                                        F       CH.sub.3                                                                                 ##STR532##   H      H                                        H       H                                                                                        ##STR533##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR534##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR535##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR536##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR537##   H      H                                        F       H                                                                                        ##STR538##   H      H                                        H       CH.sub.3                                                                                 ##STR539##   H      H                                        F       CH.sub.3                                                                                 ##STR540##   H      H                                        H       H                                                                                        ##STR541##   H      H                                        F       H                                                                                        ##STR542##   H      H                                        H       CH.sub.3                                                                                 ##STR543##   H      H                                        F       CH.sub.3                                                                                 ##STR544##   H      H                                        H       H                                                                                        ##STR545##   H      H                                        F       H                                                                                        ##STR546##   H      H                                        H       CH.sub.3                                                                                 ##STR547##   H      H                                        F       CH.sub.3                                                                                 ##STR548##   H      H                                        H       H                                                                                        ##STR549##   H      H                                        F       H                                                                                        ##STR550##   H      H                                        H       CH.sub.3                                                                                 ##STR551##   H      H                                        F       CH.sub.3                                                                                 ##STR552##   H      H                                        H       H                                                                                        ##STR553##   H      H                                        F       H                                                                                        ##STR554##   H      H                                        H       CH.sub.3                                                                                 ##STR555##   H      H                                        F       CH.sub.3                                                                                 ##STR556##   H      H                                        H       H                                                                                        ##STR557##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR558##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR559##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR560##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR561##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR562##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR563##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR564##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR565##   H      H                                        F       H                                                                                        ##STR566##   H      H                                        H       CH.sub.3                                                                                 ##STR567##   H      H                                        F       CH.sub.3                                                                                 ##STR568##   H      H                                        H       H                                                                                        ##STR569##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR570##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR571##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR572##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR573##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR574##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR575##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR576##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR577##   H      H                                        F       H                                                                                        ##STR578##   H      H                                        H       CH.sub.3                                                                                 ##STR579##   H      H                                        F       CH.sub.3                                                                                 ##STR580##   H      H                                        H       H                                                                                        ##STR581##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR582##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR583##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR584##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR585##   H      H                                        F       H                                                                                        ##STR586##   H      H                                        F       CH.sub.3                                                                                 ##STR587##   H      H                                        F       CH.sub.3                                                                                 ##STR588##   H      H                                        H       H                                                                                        ##STR589##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR590##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR591##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR592##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR593##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR594##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR595##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR596##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR597##   H      H                                        F       H                                                                                        ##STR598##   H      H                                        H       CH.sub.3                                                                                 ##STR599##   H      H                                        F       CH.sub.3                                                                                 ##STR600##   H      H                                        H       H                                                                                        ##STR601##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR602##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR603##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR604##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR605##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR606##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR607##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR608##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR609##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR610##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR611##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR612##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR613##   H      H                                        F       H                                                                                        ##STR614##   H      H                                        H       CH.sub.3                                                                                 ##STR615##   H      H                                        F       CH.sub.3                                                                                 ##STR616##   H      H                                        H       H                                                                                        ##STR617##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR618##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR619##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR620##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR621##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR622##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR623##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR624##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR625##   H      H                                        F       H                                                                                        ##STR626##   H      H                                        H       CH.sub.3                                                                                 ##STR627##   H      H                                        F       CH.sub.3                                                                                 ##STR628##   H      H                                        H       H                                                                                        ##STR629##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR630##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR631##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR632##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR633##   H      H                                        F       H                                                                                        ##STR634##   H      H                                        H       CH.sub.3                                                                                 ##STR635##   H      H                                        F       CH.sub.3                                                                                 ##STR636##   H      H                                        H       H                                                                                        ##STR637##   CH.sub.3                                                                              H                                        F       H                                                                                        ##STR638##   CH.sub.3                                                                              H                                        H       CH.sub.3                                                                                 ##STR639##   CH.sub.3                                                                              H                                        F       CH.sub.3                                                                                 ##STR640##   CH.sub.3                                                                              H                                        H       H                                                                                        ##STR641##   CH.sub.3                                                                              CH.sub.3                                 F       H                                                                                        ##STR642##   CH.sub.3                                                                              CH.sub.3                                 H       CH.sub.3                                                                                 ##STR643##   CH.sub.3                                                                              CH.sub.3                                 F       CH.sub.3                                                                                 ##STR644##   CH.sub.3                                                                              CH.sub.3                                 H       H                                                                                        ##STR645##   H      H                                        F       H                                                                                        ##STR646##   H      H                                        H       CH.sub.3                                                                                 ##STR647##   H      H                                        F       CH.sub.3                                                                                 ##STR648##   H      H                                        H       H                                                                                        ##STR649##   H      H                                        F       H                                                                                        ##STR650##   H      H                                        H       CH.sub.3                                                                                 ##STR651##   H      H                                        F       CH.sub.3                                                                                 ##STR652##   H      H                                        H       H                                                                                        ##STR653##   H      H                                        F       H                                                                                        ##STR654##   H      H                                        H       CH.sub.3                                                                                 ##STR655##   H      H                                        F       CH.sub.3                                                                                 ##STR656##   H      H                                        ______________________________________                                    

                  TABLE IIIa                                                       ______________________________________                                          ##STR657##                                                                    R.sup.1  R.sup.4  R.sup.5  A                                                   ______________________________________                                         H        H        H        H                                                   F        H        H        H                                                   H        CH.sub.3 H        H                                                   F        CH.sub.3 H        H                                                   H        H        H        CH.sub.3                                            F        H        H        CH.sub.3                                            H        CH.sub.3 H        CH.sub.3                                            F        CH.sub.3 H        CH.sub.3                                            H        H        H        CH.sub.2 CH.sub.3                                   F        H        H        CH.sub.2 CH.sub.3                                   H        CH.sub.3 H        CH.sub.2 CH.sub.3                                   F        CH.sub.3 H        CH.sub.2 CH.sub.3                                   H        H        H        CH(CH.sub.3).sub.2                                  F        H        H        CH(CH.sub.3).sub.2                                  H        CH.sub.3 H        CH(CH.sub.3).sub.2                                  F        CH.sub.3 H        CH(CH.sub.3).sub.2                                  H        H        H        CH.sub.2 CHCH.sub.2                                 F        H        H        CH.sub.2 CHCH.sub.2                                 H        CH.sub.3 H        CH.sub.2 CHCH.sub.2                                 F        CH.sub.3 H        CH.sub.2 CHCH.sub.2                                 H        H        H        CH.sub.2 CHCHCH.sub.3                               F        H        H        CH.sub.2 CHCHCH.sub.3                               H        CH.sub.3 H        CH.sub.2 CHCHCH.sub.3                               F        CH.sub.3 H        CH.sub.2 CHCHCH.sub.3                               H        H        H        CH.sub.2 CHCH                                       F        H        H        CH.sub.2 CHCH                                       H        CH.sub.3 H        CH.sub.2 CHCH                                       F        CH.sub.3 H        CH.sub.2 CHCH                                       H        H        H        CH.sub.2 CCCH.sub.3                                 F        H        H        CH.sub.2 CCCH.sub.3                                 H        CH.sub.3 H        CH.sub.2 CCCH.sub.3                                 F        CH.sub.3 H        CH.sub.2 CCCH.sub.3                                 H        H        H        CH.sub.2 OCH.sub.3                                  F        H        H        CH.sub.2 OCH.sub.3                                  H        CH.sub.3 H        CH.sub.2 OCH.sub. 3                                 F        CH.sub.3 H        CH.sub.2 OCH.sub.3                                  H        H        H        (CH.sub.2).sub.2 OCH.sub.3                          F        H        H        (CH.sub.2).sub.2 OCH.sub.3                          H        CH.sub.3 H        (CH.sub.2).sub.2 OCH.sub.3                          F        CH.sub.3 H        (CH.sub.2).sub.2 OCH.sub.3                          H        H        H        CH.sub.2 CO.sub.2 CH.sub.3                          F        H        H        CH.sub.2 CO.sub.2 CH.sub.3                          H        CH.sub.3 H        CH.sub.2 CO.sub.2 CH.sub.3                          F        CH.sub.3 H        CH.sub.2 CO.sub.2 CH.sub.3                          H        H        H        CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                 F        H        H        CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                 H        CH.sub.3 H        CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                 F        CH.sub.3 H        CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                 H        H        H        CH(CH.sub.3)CO.sub.2 CH.sub.3                       F        H        H        CH(CH.sub.3)CO.sub.2 CH.sub.3                       H        CH.sub.3 H        CH(CH.sub.3)CO.sub.2 CH.sub.3                       F        CH.sub.3 H        CH(CH.sub.3)CO.sub.2 CH.sub.3                       H        H        H        CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3              F        H        H        CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3              H        CH.sub.3 H        CH(CH.sub.3)CO.sub.2 CH.sub. 2 CH.sub.3             F        CH.sub.3 H        CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3              H        CH.sub.3 CH.sub.3 H                                                   F        CH.sub.3 CH.sub.3 H                                                   H        CH.sub.3 CH.sub.3 CH.sub.3                                            F        CH.sub.3 CH.sub.3 CH.sub.3                                            H        CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.3                                   F        CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.3                                   H        CH.sub.3 CH.sub.3 CH.sub.2 CHCH.sub.2                                 F        CH.sub.3 CH.sub.3 CH.sub.2 CHCH.sub.2                                 H        CH.sub.3 CH.sub.3 CH.sub.2 CCH                                        F        CH.sub.3 CH.sub.3 CH.sub.2 CCH                                        H        CH.sub.3 CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3                          F        CH.sub.3 CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3                          H        CH.sub.3 CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3                          F        CH.sub.3 CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3                          H        CH.sub.3 CH.sub.3 CH(CH.sub.3)CO.sub.2 CH.sub.3                       F        CH.sub.3 CH.sub.3 CH(CH.sub.3)CO.sub.2 CH.sub.3                       ______________________________________                                    

                  TABLE IV                                                         ______________________________________                                          ##STR658##                                                                    R.sup.1      R.sup.2    R.sup.3                                                ______________________________________                                         H            H                                                                                          ##STR659##                                            F            H                                                                                          ##STR660##                                            H            CH.sub.3                                                                                   ##STR661##                                            F            CH.sub.3                                                                                   ##STR662##                                            H            H                                                                                          ##STR663##                                            F            H                                                                                          ##STR664##                                            H            CH.sub.3                                                                                   ##STR665##                                            F            CH.sub.3                                                                                   ##STR666##                                            H            H                                                                                          ##STR667##                                            F            H                                                                                          ##STR668##                                            H            CH.sub.3                                                                                   ##STR669##                                            F            CH.sub.3                                                                                   ##STR670##                                            H            H                                                                                          ##STR671##                                            F            H                                                                                          ##STR672##                                            H            CH.sub.3                                                                                   ##STR673##                                            F            CH.sub.3                                                                                   ##STR674##                                            H            H                                                                                          ##STR675##                                            F            H                                                                                          ##STR676##                                            H            CH.sub.3                                                                                   ##STR677##                                            F            CH.sub.3                                                                                   ##STR678##                                            H            H                                                                                          ##STR679##                                            F            H                                                                                          ##STR680##                                            H            CH.sub.3                                                                                   ##STR681##                                            F            CH.sub.3                                                                                   ##STR682##                                            H            H                                                                                          ##STR683##                                            F            H                                                                                          ##STR684##                                            H            CH.sub.3                                                                                   ##STR685##                                            F            CH.sub.3                                                                                   ##STR686##                                            H            H                                                                                          ##STR687##                                            F            H                                                                                          ##STR688##                                            H            CH.sub.3                                                                                   ##STR689##                                            F            CH.sub.3                                                                                   ##STR690##                                            H            H                                                                                          ##STR691##                                            F            H                                                                                          ##STR692##                                            H            CH.sub.3                                                                                   ##STR693##                                            F            CH.sub.3                                                                                   ##STR694##                                            H            H                                                                                          ##STR695##                                            F            H                                                                                          ##STR696##                                            H            CH.sub.3                                                                                   ##STR697##                                            F            CH.sub.3                                                                                   ##STR698##                                            H            H                                                                                          ##STR699##                                            F            H                                                                                          ##STR700##                                            H            CH.sub.3                                                                                   ##STR701##                                            F            CH.sub.3                                                                                   ##STR702##                                            H            H                                                                                          ##STR703##                                            F            H                                                                                          ##STR704##                                            H            CH.sub.3                                                                                   ##STR705##                                            F            CH.sub.3                                                                                   ##STR706##                                            H            H                                                                                          ##STR707##                                            F            H                                                                                          ##STR708##                                            H            CH.sub.3                                                                                   ##STR709##                                            F            CH.sub.3                                                                                   ##STR710##                                            H            H                                                                                          ##STR711##                                            F            H                                                                                          ##STR712##                                            H            CH.sub.3                                                                                   ##STR713##                                            F            CH.sub.3                                                                                   ##STR714##                                            H            H                                                                                          ##STR715##                                            F            H                                                                                          ##STR716##                                            H            CH.sub.3                                                                                   ##STR717##                                            F            CH.sub.3                                                                                   ##STR718##                                            H            H                                                                                          ##STR719##                                            F            H                                                                                          ##STR720##                                            H            CH.sub.3                                                                                   ##STR721##                                            F            CH.sub.3                                                                                   ##STR722##                                            H            H                                                                                          ##STR723##                                            F            H                                                                                          ##STR724##                                            H            CH.sub.3                                                                                   ##STR725##                                            F            CH.sub.3                                                                                   ##STR726##                                            H            H                                                                                          ##STR727##                                            F            H                                                                                          ##STR728##                                            H            CH.sub.3                                                                                   ##STR729##                                            F            CH.sub.3                                                                                   ##STR730##                                            H            H                                                                                          ##STR731##                                            F            H                                                                                          ##STR732##                                            H            CH.sub.3                                                                                   ##STR733##                                            F            CH.sub.3                                                                                   ##STR734##                                            H            H                                                                                          ##STR735##                                            F            H                                                                                          ##STR736##                                            H            CH.sub.3                                                                                   ##STR737##                                            F            CH.sub.3                                                                                   ##STR738##                                            H            H                                                                                          ##STR739##                                            F            H                                                                                          ##STR740##                                            H            CH.sub.3                                                                                   ##STR741##                                            F            CH.sub.3                                                                                   ##STR742##                                            H            H                                                                                          ##STR743##                                            F            H                                                                                          ##STR744##                                            H            CH.sub.3                                                                                   ##STR745##                                            F            CH.sub.3                                                                                   ##STR746##                                            H            H                                                                                          ##STR747##                                            F            H                                                                                          ##STR748##                                            H            CH.sub.3                                                                                   ##STR749##                                            F            CH.sub.3                                                                                   ##STR750##                                            H            H                                                                                          ##STR751##                                            F            H                                                                                          ##STR752##                                            H            CH.sub.3                                                                                   ##STR753##                                            F            CH.sub.3                                                                                   ##STR754##                                            H            H                                                                                          ##STR755##                                            F            H                                                                                          ##STR756##                                            H            CH.sub.3                                                                                   ##STR757##                                            F            CH.sub.3                                                                                   ##STR758##                                            H            H                                                                                          ##STR759##                                            F            H                                                                                          ##STR760##                                            H            CH.sub.3                                                                                   ##STR761##                                            F            CH.sub.3                                                                                   ##STR762##                                            ______________________________________                                    

                  TABLE IVa                                                        ______________________________________                                          ##STR763##                                                                    R.sup.1         A                                                              ______________________________________                                         H               H                                                              F               H                                                              H               CH.sub.3                                                       F               CH.sub.3                                                       H               CH.sub.2 CH.sub.3                                              F               CH.sub.2 CH.sub.3                                              H               CH(CH.sub.3).sub.2                                             F               CH(CH.sub.3).sub.2                                             H               CH.sub.2 CHCH.sub.2                                            F               CH.sub.2 CHCH.sub.2                                            H               CH.sub.2 CHCHCH.sub.3                                          F               CH.sub.2 CHCHCH.sub.3                                          H               CH.sub.2 CCH                                                   F               CH.sub.2 CCH                                                   H               CH.sub.2 CCCH.sub.3                                            F               CH.sub.2 CCCH.sub.3                                            H               CH.sub.2 OCH.sub.3                                             F               CH.sub.2 OCH.sub.3                                             H               (CH.sub.2).sub.2 OCH.sub.3                                     F               (CH.sub.2).sub.2 OCH.sub.3                                     H               CH.sub.2 CO.sub.2 CH.sub. 3                                    F               CH.sub.2 CO.sub.2 CH.sub.3                                     H               CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                            F               CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                            H               CH(CH.sub.3)CO.sub.2 CH.sub.3                                  F               CH(CH.sub.3)CO.sub.2 CH.sub.3                                  H               CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                         F               CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                         ______________________________________                                    

                  TABLE V                                                          ______________________________________                                          ##STR764##                                                                    R.sup.1      R.sup.2    R.sup.3                                                ______________________________________                                         H            H                                                                                          ##STR765##                                            F            H                                                                                          ##STR766##                                            H            CH.sub.3                                                                                   ##STR767##                                            F            CH.sub.3                                                                                   ##STR768##                                            H            H                                                                                          ##STR769##                                            F            H                                                                                          ##STR770##                                            H            CH.sub.3                                                                                   ##STR771##                                            F            CH.sub.3                                                                                   ##STR772##                                            H            H                                                                                          ##STR773##                                            F            H                                                                                          ##STR774##                                            H            CH.sub.3                                                                                   ##STR775##                                            F            CH.sub.3                                                                                   ##STR776##                                            H            H                                                                                          ##STR777##                                            F            H                                                                                          ##STR778##                                            H            CH.sub.3                                                                                   ##STR779##                                            F            CH.sub.3                                                                                   ##STR780##                                            H            H                                                                                          ##STR781##                                            F            H                                                                                          ##STR782##                                            H            CH.sub.3                                                                                   ##STR783##                                            F            CH.sub.3                                                                                   ##STR784##                                            H            H                                                                                          ##STR785##                                            F            H                                                                                          ##STR786##                                            H            CH.sub.3                                                                                   ##STR787##                                            F            CH.sub.3                                                                                   ##STR788##                                            H            H                                                                                          ##STR789##                                            F            H                                                                                          ##STR790##                                            H            CH.sub.3                                                                                   ##STR791##                                            F            CH.sub.3                                                                                   ##STR792##                                            H            H                                                                                          ##STR793##                                            F            H                                                                                          ##STR794##                                            H            CH.sub.3                                                                                   ##STR795##                                            F            CH.sub.3                                                                                   ##STR796##                                            H            H                                                                                          ##STR797##                                            F            H                                                                                          ##STR798##                                            H            CH.sub.3                                                                                   ##STR799##                                            F            CH.sub.3                                                                                   ##STR800##                                            H            H                                                                                          ##STR801##                                            F            H                                                                                          ##STR802##                                            H            CH.sub.3                                                                                   ##STR803##                                            F            CH.sub.3                                                                                   ##STR804##                                            H            H                                                                                          ##STR805##                                            F            H                                                                                          ##STR806##                                            H            CH.sub.3                                                                                   ##STR807##                                            F            CH.sub.3                                                                                   ##STR808##                                            H            H                                                                                          ##STR809##                                            F            H                                                                                          ##STR810##                                            H            CH.sub.3                                                                                   ##STR811##                                            F            CH.sub.3                                                                                   ##STR812##                                            H            H                                                                                          ##STR813##                                            F            H                                                                                          ##STR814##                                            H            CH.sub.3                                                                                   ##STR815##                                            F            CH.sub.3                                                                                   ##STR816##                                            H            H                                                                                          ##STR817##                                            F            H                                                                                          ##STR818##                                            H            CH.sub.3                                                                                   ##STR819##                                            F            CH.sub.3                                                                                   ##STR820##                                            H            H                                                                                          ##STR821##                                            F            H                                                                                          ##STR822##                                            H            CH.sub.3                                                                                   ##STR823##                                            F            CH.sub.3                                                                                   ##STR824##                                            H            H                                                                                          ##STR825##                                            F            H                                                                                          ##STR826##                                            H            CH.sub.3                                                                                   ##STR827##                                            F            CH.sub.3                                                                                   ##STR828##                                            H            H                                                                                          ##STR829##                                            F            H                                                                                          ##STR830##                                            H            CH.sub.3                                                                                   ##STR831##                                            F            CH.sub.3                                                                                   ##STR832##                                            H            H                                                                                          ##STR833##                                            F            H                                                                                          ##STR834##                                            H            CH.sub.3                                                                                   ##STR835##                                            F            CH.sub.3                                                                                   ##STR836##                                            H            H                                                                                          ##STR837##                                            F            H                                                                                          ##STR838##                                            H            CH.sub.3                                                                                   ##STR839##                                            F            CH.sub.3                                                                                   ##STR840##                                            H            H                                                                                          ##STR841##                                            F            H                                                                                          ##STR842##                                            H            CH.sub.3                                                                                   ##STR843##                                            F            CH.sub.3                                                                                   ##STR844##                                            H            H                                                                                          ##STR845##                                            F            H                                                                                          ##STR846##                                            H            CH.sub.3                                                                                   ##STR847##                                            F            CH.sub.3                                                                                   ##STR848##                                            H            H                                                                                          ##STR849##                                            F            H                                                                                          ##STR850##                                            H            CH.sub.3                                                                                   ##STR851##                                            F            CH.sub.3                                                                                   ##STR852##                                            H            H                                                                                          ##STR853##                                            F            H                                                                                          ##STR854##                                            H            CH.sub.3                                                                                   ##STR855##                                            F            CH.sub.3                                                                                   ##STR856##                                            H            H                                                                                          ##STR857##                                            F            H                                                                                          ##STR858##                                            H            CH.sub.3                                                                                   ##STR859##                                            F            CH.sub.3                                                                                   ##STR860##                                            H            H                                                                                          ##STR861##                                            F            H                                                                                          ##STR862##                                            H            CH.sub.3                                                                                   ##STR863##                                            F            CH.sub.3                                                                                   ##STR864##                                            H            H                                                                                          ##STR865##                                            F            H                                                                                          ##STR866##                                            H            CH.sub.3                                                                                   ##STR867##                                            F            CH.sub.3                                                                                   ##STR868##                                            ______________________________________                                    

                  TABLE VI                                                         ______________________________________                                          ##STR869##                                                                    R.sup.1      R.sup.2    R.sup.3                                                ______________________________________                                         H            H                                                                                          ##STR870##                                            F            H                                                                                          ##STR871##                                            H            CH.sub.3                                                                                   ##STR872##                                            F            CH.sub.3                                                                                   ##STR873##                                            H            H                                                                                          ##STR874##                                            F            H                                                                                          ##STR875##                                            H            CH.sub.3                                                                                   ##STR876##                                            F            CH.sub.3                                                                                   ##STR877##                                            H            H                                                                                          ##STR878##                                            F            H                                                                                          ##STR879##                                            H            CH.sub.3                                                                                   ##STR880##                                            F            CH.sub.3                                                                                   ##STR881##                                            H            H                                                                                          ##STR882##                                            F            H                                                                                          ##STR883##                                            H            CH.sub.3                                                                                   ##STR884##                                            F            CH.sub.3                                                                                   ##STR885##                                            H            H                                                                                          ##STR886##                                            F            H                                                                                          ##STR887##                                            H            CH.sub.3                                                                                   ##STR888##                                            F            CH.sub.3                                                                                   ##STR889##                                            H            H                                                                                          ##STR890##                                            F            H                                                                                          ##STR891##                                            H            CH.sub.3                                                                                   ##STR892##                                            F            CH.sub.3                                                                                   ##STR893##                                            H            H                                                                                          ##STR894##                                            F            H                                                                                          ##STR895##                                            H            CH.sub.3                                                                                   ##STR896##                                            F            CH.sub.3                                                                                   ##STR897##                                            H            H                                                                                          ##STR898##                                            F            H                                                                                          ##STR899##                                            H            CH.sub.3                                                                                   ##STR900##                                            F            CH.sub.3                                                                                   ##STR901##                                            H            H                                                                                          ##STR902##                                            F            H                                                                                          ##STR903##                                            H            CH.sub.3                                                                                   ##STR904##                                            F            CH.sub.3                                                                                   ##STR905##                                            H            H                                                                                          ##STR906##                                            F            H                                                                                          ##STR907##                                            H            CH.sub.3                                                                                   ##STR908##                                            F            CH.sub.3                                                                                   ##STR909##                                            H            H                                                                                          ##STR910##                                            F            H                                                                                          ##STR911##                                            H            CH.sub.3                                                                                   ##STR912##                                            F            CH.sub.3                                                                                   ##STR913##                                            H            H                                                                                          ##STR914##                                            F            H                                                                                          ##STR915##                                            H            CH.sub.3                                                                                   ##STR916##                                            F            CH.sub.3                                                                                   ##STR917##                                            H            H                                                                                          ##STR918##                                            F            H                                                                                          ##STR919##                                            H            CH.sub.3                                                                                   ##STR920##                                            F            CH.sub.3                                                                                   ##STR921##                                            H            H                                                                                          ##STR922##                                            F            H                                                                                          ##STR923##                                            H            CH.sub.3                                                                                   ##STR924##                                            F            CH.sub.3                                                                                   ##STR925##                                            H            H                                                                                          ##STR926##                                            F            H                                                                                          ##STR927##                                            H            CH.sub.3                                                                                   ##STR928##                                            F            CH.sub.3                                                                                   ##STR929##                                            H            H                                                                                          ##STR930##                                            F            H                                                                                          ##STR931##                                            H            CH.sub.3                                                                                   ##STR932##                                            F            CH.sub.3                                                                                   ##STR933##                                            H            H                                                                                          ##STR934##                                            F            H                                                                                          ##STR935##                                            H            CH.sub.3                                                                                   ##STR936##                                            F            CH.sub.3                                                                                   ##STR937##                                            H            H                                                                                          ##STR938##                                            F            H                                                                                          ##STR939##                                            H            CH.sub.3                                                                                   ##STR940##                                            F            CH.sub.3                                                                                   ##STR941##                                            H            H                                                                                          ##STR942##                                            F            H                                                                                          ##STR943##                                            H            CH.sub.3                                                                                   ##STR944##                                            F            CH.sub.3                                                                                   ##STR945##                                            H            H                                                                                          ##STR946##                                            F            H                                                                                          ##STR947##                                            H            CH.sub.3                                                                                   ##STR948##                                            F            CH.sub.3                                                                                   ##STR949##                                            H            H                                                                                          ##STR950##                                            F            H                                                                                          ##STR951##                                            H            CH.sub.3                                                                                   ##STR952##                                            F            CH.sub.3                                                                                   ##STR953##                                            H            H                                                                                          ##STR954##                                            F            H                                                                                          ##STR955##                                            H            CH.sub.3                                                                                   ##STR956##                                            F            CH.sub.3                                                                                   ##STR957##                                            H            H                                                                                          ##STR958##                                            F            H                                                                                          ##STR959##                                            H            CH.sub.3                                                                                   ##STR960##                                            F            CH.sub.3                                                                                   ##STR961##                                            H            H                                                                                          ##STR962##                                            F            H                                                                                          ##STR963##                                            H            CH.sub.3                                                                                   ##STR964##                                            F            CH.sub.3                                                                                   ##STR965##                                            H            H                                                                                          ##STR966##                                            F            H                                                                                          ##STR967##                                            H            CH.sub.3                                                                                   ##STR968##                                            F            CH.sub.3                                                                                   ##STR969##                                            H            H                                                                                          ##STR970##                                            F            H                                                                                          ##STR971##                                            H            CH.sub.3                                                                                   ##STR972##                                            F            CH.sub.3                                                                                   ##STR973##                                            ______________________________________                                    

The N-aryltetrahydrophthalimide compounds I, or herbicidal agents containing them, may be applied for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used, but they must ensure as fine a distribution of the active ingredients according to the invention as possible.

For the preparation of solutions, emulsions, pastes and oil dispersions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils, and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc. are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions or wettable powders by adding water. To prepare emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.

Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal slats of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulfite waste liquors and methyl cellulose.

Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acid, silica gels, silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.

The formulations contain from 0.1 to 95, and preferably 0.5 to 90% by weight of active ingredient.

Examples of formulations are given below.

I. 90 parts by weight of compound no. 1.003 is mixed with 10 parts by weight of N-methyl-alpha-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

II. 20 parts by weight of compound no. 1.011 is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzene-sulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

III. 20 parts by weight of compound no. 1.035 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol, and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

IV. 20 parts by weight of compound no. 3.059 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

In view of the number of application methods available the compounds according to the invention, or agents containing them, may be used in a further large number of crop plants for combating unwanted plants. Examples of such crops are as follows:

V. 20 parts by weight of compound no. 4.047 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 17 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained containing 0.1% by weight of the active ingredient.

VI. 3 parts by weight of compound no. 1.023 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient.

VII. 30 parts by weight of compound no. 1.033 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

VIII. 20 parts of compound no. 3.067 is intimately mixed with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.

The herbicidal agents, or the active ingredients on which they are based, may be applied pre- or postemergence. If certain crop plants tolerate the active ingredients less well, application techniques may be used in which the herbicidal agents are sprayed from suitable equipment in such a manner that the leaves of sensitive crop plants are if possible not touched, and the agents reach the soil or the unwanted plants growing beneath the crop plants (post-directed, lay-by treatment).

The application rates depend on the objective to be achieved, the time of the year, the plants to be combated and their growth stage, and are from 0.001 to 5.0, preferably 0.01 to 0.5, kg/ha.

In view of the number of application methods available the compounds according to the invention, or agents containing them, may be used in a further large number of crop plants for combating unwanted plants. Examples of such crops are as follows:

    ______________________________________                                         Botanical Name       Common Name                                               ______________________________________                                         Allium cepa          onions                                                    Ananas comosus       pineapples                                                Arachis hypogaea     peanuts (groundnuts)                                      Asparagus officinalis                                                                               asparagus                                                 Avena sativa         oats                                                      Beta vulgaris spp. altissima                                                                        sugarbeets                                                Beta vulgaris spp. rapa                                                                             fodder beets                                              Beta vulgaris spp. esculenta                                                                        table beets, red beets                                    Brassica napus var. napus                                                                           rapeseed                                                  Brassica napus var. napobrassica                                                                    swedes                                                    Brassica napus var. rapa                                                                            turnips                                                   Brassica rapa var. silvestris                                                  Camellia sinensis    tea plants                                                Carthamus tinctorius safflower                                                 Carya illinoinensis  pecan trees                                               Citrus limon         lemons                                                    Citrus maxima        grapefruits                                               Citrus reticulata    mandarins                                                 Citrus sinensis      orange trees                                              Coffea arabica (Coffea canephora,                                                                   coffee plants                                             Coffea liberica)                                                               Cucumis melo         melons                                                    Cucumis sativus      cucumbers                                                 Cynodon dactylon     Bermudagrass                                              Daucus carota        carrots                                                   Elais guineensis     oil palms                                                 Fragaria vesca       strawberries                                              Glycine max          soybeans                                                  Gossypium hirsutum (Gossypium                                                                       cotton                                                    arboreum, Gossypium herbaceum,                                                 Gossypium vitifolium)                                                          Helianthus annuus    sunflowers                                                Helianthus tuberosus Jerusalem artichoke                                       Hevea brasiliensis   rubber plants                                             Hordeum vulgare      barley                                                    Humulus lupulus      hops                                                      Ipomoea batatas      sweet potatoes                                            Juglans regia        walnut trees                                              Lactuca sativa       lettuce                                                   Lens culinaris       lentils                                                   Linum usitatissimum  flax                                                      Lycopersicon lycopersicum                                                                           tomatoes                                                  Malus spp.           apple trees                                               Manihot esculenta    cassava                                                   Medicago sativa      alfalfa (lucerne)                                         Mentha piperita      peppermint                                                Musa spp.            banana plants                                             Nicotiana tabacum (N. rustica)                                                                      tobacco                                                   Olea europaea        olive trees                                               Oryza sativa         rice                                                      Phaseolus lunatus    limabeans                                                 Phaseolus mungo      mungbeans                                                 Phaseolus vulgaris   snapbeans, green beans,                                                        dry beans                                                 Pennisetum glaucum   pearl millet                                              Petroselinum crispum spp. tuberosum                                                                 parsley                                                   Picea abies          Norway spruce                                             Abies alba           fir trees                                                 Pinus spp.           pine trees                                                Pisum sativum        English peas                                              Prunus avium         cherry trees                                              Prunus domestica     plum trees                                                Prunus dulcis        almond trees                                              Prunus persica       peach trees                                               Pyrus communis       pear trees                                                Ribes sylvestre      redcurrants                                               Ribes uva-crispa     gooseberries                                              Ricinus communis     castor-oil plants                                         Saccharum officinarum                                                                               sugar cane                                                Secale cereale       rye                                                       Sesamum indicum      sesame                                                    Solanum tuberosum    Irish potatoes                                            Sorghum bicolor (S. vulgare)                                                                        sorghum                                                   Sorghum dochna       sorgo                                                     Spinacia oleracea    spinach                                                   Theobroma cacao      cacao plants                                              Trifolium pratense   red clover                                                Triticum aestivum    wheat                                                     Triticum durum       durum wheat                                               Vaccinium corymbosum blueberries                                               Vaccinium vitis-idaea                                                                               cranberries                                               Vicia faba           tick beans                                                Vigna sinensis (V. unguiculata)                                                                     cow peas                                                  Vitis vinifera       grapes                                                    Zea mays             Indian corn, sweet corn,                                                       maize                                                     ______________________________________                                    

To increase the spectrum of action and to achieve synergistic effects, the N-aryltetrahydrophthalimide compounds of the formula I may be mixed and applied togethr with numerous representatives of other herbicidal or growth-regulating active ingredient groups. Examples of suitable components are diazines, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, thiolcarbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane-1,3-dione derivatives, quinolinecarboxylic acids, phenyloxy- or heteroaryloxy-phenylpropionic acids and salts, esters and amides thereof, etc.

It may also be useful to apply the novel compounds of the formula I, either alone or in combination with other herbicides, in admixture with other crop protection agents, e.g., agents for combating pests or phytopathogenic fungi or bacteria. The compounds may also be mixed with solutions of mineral salts used to remedy nutritional or trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.

SYNTHESIS EXAMPLES Example 1 ##STR974##

a) 4.9 g (0.03 mol) of 6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one is introduced into 50 ml of dimethylformamide. At 5° C., 0.79 g (0.033 mol) of sodium hydride is added, and the mixture is stirred for 30 minutes at this temperature. Subsequently, 5.9 g (0.033 mol) of 4-bromomethyltetrahydropyran is added, the mixture is stirred for 3 hours at 60° C., 200 ml of water is added, extraction is carried out twice with methylene chloride, followed by drying and evaporation of the solvent under reduced pressure. There is obtained 5 g (64%) of 4-(tetrahydropyran-4-ylmethyl)-6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one as an oil.

b) 4.5 g (0.017 mol) of the abovementioned aniline and 2.7 g (0.018 mol) of cyclohexene-1,2-dicarboxylic anhydride are stirred for 3 hours at 70° C. in 70 ml of glacial acetic acid. After the mixture has cooled, 100 ml of water is added and the mixture filtered. The precipitate is washed with water and dried. There is obtained 3.5 g (52%) of N-[4-(tetrahydropyran-4-ylmethyl)-3,4-dihydro-2H-1,4-benzoxazin-3-on-6-yl]-3,4,5,6-tetrahydrophthalimide (m.p. 187°-189° C.) (Table 1, No. 1.033).

                  TABLE 1                                                          ______________________________________                                          ##STR975##                I                                                   No.   R.sup.1                                                                               R.sup.2 R.sup.3  R.sup.4                                                                              R.sup.5                                                                             m.p.[°C.]                      ______________________________________                                         1.001 H      H                                                                                       ##STR976##                                                                             H     H                                          1.002 F      H                                                                                       ##STR977##                                                                             H     H                                          1.003 H      H                                                                                       ##STR978##                                                                             H     H    165-166                               1.004 F      H                                                                                       ##STR979##                                                                             H     H    204-206                               1.005 H      H                                                                                       ##STR980##                                                                             CH.sub.3                                                                             H                                          1.006 F      H                                                                                       ##STR981##                                                                             CH.sub.3                                                                             H                                          1.007 H      H                                                                                       ##STR982##                                                                             H     H                                          1.008 F      H                                                                                       ##STR983##                                                                             H     H                                          1.009 H      H                                                                                       ##STR984##                                                                             H     H                                          1.010 F      H                                                                                       ##STR985##                                                                             H     H                                          1.011 H      H                                                                                       ##STR986##                                                                             H     H    140-142                               1.012 F      H                                                                                       ##STR987##                                                                             H     H                                          1.013 H      H                                                                                       ##STR988##                                                                             CH.sub.3                                                                             H                                          1.014 F      H                                                                                       ##STR989##                                                                             CH.sub.3                                                                             H                                          1.015 H      H                                                                                       ##STR990##                                                                             H     H                                          1.016 F      H                                                                                       ##STR991##                                                                             H     H                                          1.017 H      H                                                                                       ##STR992##                                                                             H     H                                          1.018 F      H                                                                                       ##STR993##                                                                             H     H                                          1.019 H      H                                                                                       ##STR994##                                                                             H     H                                          1.020 F      H                                                                                       ##STR995##                                                                             H     H                                          1.021 H      H                                                                                       ##STR996##                                                                             H     H                                          1.022 F      H                                                                                       ##STR997##                                                                             H     H                                          1.023 H      H                                                                                       ##STR998##                                                                             H     H    145-147                               1.024 F      H                                                                                       ##STR999##                                                                             H     H                                          1.025 H      H                                                                                       ##STR1000##                                                                            CH.sub.3                                                                             H                                          1.026 F      H                                                                                       ##STR1001##                                                                            CH.sub.3                                                                             H                                          1.027 H      H                                                                                       ##STR1002##                                                                            H     H    138-140                               1.028 F      H                                                                                       ##STR1003##                                                                            H     H    70 (Zers.)                            1.029 H      H                                                                                       ##STR1004##                                                                            CH.sub.3                                                                             H    145-147                               1.030 F      H                                                                                       ##STR1005##                                                                            CH.sub.3                                                                             H                                          1.031 H      CH.sub.3                                                                                ##STR1006##                                                                            H     H                                          1.032 F      CH.sub.3                                                                                ##STR1007##                                                                            H     H                                          1.033 H      H                                                                                       ##STR1008##                                                                            H     H    187-189                               1.034 F      H                                                                                       ##STR1009##                                                                            H     H                                          1.035 H      H                                                                                       ##STR1010##                                                                            CH.sub.3                                                                             H    150-152                               1.036 F      H                                                                                       ##STR1011##                                                                            CH.sub.3                                                                             H                                          1.037 H      H                                                                                       ##STR1012##                                                                            H     H                                          1.038 F      H                                                                                       ##STR1013##                                                                            H     H                                          1.039 H      H                                                                                       ##STR1014##                                                                            H     H                                          1.040 F      H                                                                                       ##STR1015##                                                                            H     H    178-179                               1.041 H      H                                                                                       ##STR1016##                                                                            CH.sub.3                                                                             H                                          1.042 F      H                                                                                       ##STR1017##                                                                            CH.sub.3                                                                             H                                          1.043 H      H                                                                                       ##STR1018##                                                                            H     H                                          1.044 F      H                                                                                       ##STR1019##                                                                            H     H                                          1.045 H      H                                                                                       ##STR1020##                                                                            H     H                                          1.046 F      H                                                                                       ##STR1021##                                                                            H     H                                          1.047 H      H                                                                                       ##STR1022##                                                                            H     H                                          1.048 F      H                                                                                       ##STR1023##                                                                            H     H                                          1.049 H      H                                                                                       ##STR1024##                                                                            H     H    127-129                               1.050 F      H                                                                                       ##STR1025##                                                                            H     H                                          1.051 H      H                                                                                       ##STR1026##                                                                            H     H                                          1.052 F      H                                                                                       ##STR1027##                                                                            H     H                                          1.053 H      H                                                                                       ##STR1028##                                                                            H     H    178-180                               1.054 F      H                                                                                       ##STR1029##                                                                            H     H                                          1.055 H      H                                                                                       ##STR1030##                                                                            H     H    157-168                               1.056 F      H                                                                                       ##STR1031##                                                                            H     H                                          1.057 H      H                                                                                       ##STR1032##                                                                            H     H    177-178                               1.058 F      H                                                                                       ##STR1033##                                                                            H     H                                          ______________________________________                                    

                  TABLE 2                                                          ______________________________________                                          ##STR1034##               I                                                   No.   R.sup.1                                                                               R.sup.2 R.sup.3  R.sup.4                                                                              R.sup.5                                                                             m.p.[°C.]                      ______________________________________                                         2.001 H      H                                                                                       ##STR1035##                                                                            H     H                                          2.002 F      H                                                                                       ##STR1036##                                                                            H     H                                          2.003 H      H                                                                                       ##STR1037##                                                                            H     H                                          2.004 F      H                                                                                       ##STR1038##                                                                            H     H                                          2.005 H      H                                                                                       ##STR1039##                                                                            CH.sub.3                                                                             H                                          2.006 F      H                                                                                       ##STR1040##                                                                            CH.sub.3                                                                             H                                          2.007 H      H                                                                                       ##STR1041##                                                                            H     H                                          2.008 F      H                                                                                       ##STR1042##                                                                            H     H                                          2.009 H      H                                                                                       ##STR1043##                                                                            H     H                                          2.010 F      H                                                                                       ##STR1044##                                                                            H     H                                          2.011 H      H                                                                                       ##STR1045##                                                                            H     H                                          2.012 F      H                                                                                       ##STR1046##                                                                            H     H                                          2.013 H      H                                                                                       ##STR1047##                                                                            CH.sub.3                                                                             H                                          2.014 F      H                                                                                       ##STR1048##                                                                            CH.sub.3                                                                             H                                          2.015 H      H                                                                                       ##STR1049##                                                                            H     H                                          2.016 F      H                                                                                       ##STR1050##                                                                            H     H                                          2.017 H      H                                                                                       ##STR1051##                                                                            H     H                                          2.018 F      H                                                                                       ##STR1052##                                                                            H     H                                          2.019 H      H                                                                                       ##STR1053##                                                                            H     H                                          2.020 F      H                                                                                       ##STR1054##                                                                            H     H                                          2.021 H      H                                                                                       ##STR1055##                                                                            H     H                                          2.022 F      H                                                                                       ##STR1056##                                                                            H     H                                          2.023 H      H                                                                                       ##STR1057##                                                                            H     H                                          2.024 F      H                                                                                       ##STR1058##                                                                            H     H                                          2.025 H      H                                                                                       ##STR1059##                                                                            CH.sub.3                                                                             H                                          2.026 F      H                                                                                       ##STR1060##                                                                            CH.sub.3                                                                             H                                          2.027 H      H                                                                                       ##STR1061##                                                                            H     H                                          2.028 F      H                                                                                       ##STR1062##                                                                            H     H                                          2.029 H      H                                                                                       ##STR1063##                                                                            CH.sub.3                                                                             H                                          2.030 F      H                                                                                       ##STR1064##                                                                            CH.sub.3                                                                             H                                          2.031 H      CH.sub.3                                                                                ##STR1065##                                                                            H     H                                          2.032 F      CH.sub.3                                                                                ##STR1066##                                                                            H     H                                          2.033 H      H                                                                                       ##STR1067##                                                                            H     H                                          2.034 F      H                                                                                       ##STR1068##                                                                            H     H                                          2.035 H      H                                                                                       ##STR1069##                                                                            CH.sub.3                                                                             H                                          2.036 F      H                                                                                       ##STR1070##                                                                            CH.sub.3                                                                             H                                          2.037 H      H                                                                                       ##STR1071##                                                                            H     H                                          2.038 F      H                                                                                       ##STR1072##                                                                            H     H                                          2.039 H      H                                                                                       ##STR1073##                                                                            H     H                                          2.040 F      H                                                                                       ##STR1074##                                                                            H     H                                          2.041 H      H                                                                                       ##STR1075##                                                                            CH.sub.3                                                                             H                                          2.042 F      H                                                                                       ##STR1076##                                                                            CH.sub.3                                                                             H                                          2.043 H      H                                                                                       ##STR1077##                                                                            H     H                                          2.044 F      H                                                                                       ##STR1078##                                                                            H     H                                          2.045 H      H                                                                                       ##STR1079##                                                                            H     H                                          2.046 F      H                                                                                       ##STR1080##                                                                            H     H                                          2.047 H      H                                                                                       ##STR1081##                                                                            H     H                                          2.048 F      H                                                                                       ##STR1082##                                                                            H     H                                          2.049 H      H                                                                                       ##STR1083##                                                                            H     H                                          2.050 F      H                                                                                       ##STR1084##                                                                            H     H                                          2.051 H      H                                                                                       ##STR1085##                                                                            H     H                                          2.052 F      H                                                                                       ##STR1086##                                                                            H     H                                          2.053 H      H                                                                                       ##STR1087##                                                                            H     H                                          2.054 F      H                                                                                       ##STR1088##                                                                            H     H                                          2.055 H      H                                                                                       ##STR1089##                                                                            H     H                                          2.056 F      H                                                                                       ##STR1090##                                                                            H     H                                          2.057 H      H                                                                                       ##STR1091##                                                                            H     H                                          2.058 F      H                                                                                       ##STR1092##                                                                            H     H                                          ______________________________________                                    

                  TABLE 2a                                                         ______________________________________                                          ##STR1093##               I                                                   No.   R.sup.1                                                                               A               R.sup.4                                                                             R.sup.5                                                                             m.p.[°C.]                        ______________________________________                                         2.059 H      H               H    H    230-231                                 2.060 F      H               H    H                                            2.061 H      CH.sub.3        H    H                                            2.062 F      CH.sub.3        H    H                                            2.063 H      CH.sub.2 CH.sub.3                                                                              H    H                                            2.064 F      CH.sub.2 CH.sub.3                                                                              H    H                                            2.065 H      CH(CH.sub.3).sub.2                                                                             H    H                                            2.066 F      CH(CH.sub.3).sub.2                                                                             H    H                                            2.067 H      CH.sub.2 CHCH.sub.2                                                                            H    H                                            2.068 F      CH.sub.2 CHCH.sub.2                                                                            H    H                                            2.069 H      CH.sub.2 CCH    H    H    193-194                                 2.070 F      CH.sub.2 C CH   H    H                                            2.071 H      CH.sub.2 OCH.sub.3                                                                             H    H                                            2.072 F      CH.sub.2 OCH.sub.3                                                                             H    H                                            2.073 H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                    H    H                                            2.074 F      CH.sub.2 CH.sub.2 OCH.sub.3                                                                    H    H                                            2.075 H      CH.sub.2 CO.sub.2 CH.sub.3                                                                     H    H                                            2.076 F      CH.sub.2 CO.sub.2 CH.sub.3                                                                     H    H                                            2.077 H      CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                            H    H                                            2.078 F      CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                            H    H                                            2.079 H      CH(CH.sub.3)CO.sub.2 CH.sub.3                                                                  H    H                                            2.080 F      CH(CH.sub.3)CO.sub.2 CH.sub.3                                                                  H    H                                            2.081 H      CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                         H    H                                            2.082 F      CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                         H    H                                            2.083 H      CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                         CH.sub.3                                                                            H                                            2.084 F      CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                         CH.sub.3                                                                            H                                            2.085 H      CH.sub.2 CHCH.sub.2                                                                            CH.sub.3                                                                            H                                            2.086 F      CH.sub.2 CHCH.sub.2                                                                            CH.sub.3                                                                            H                                            2.087 H      CH.sub.2 CCH    CH.sub.3                                                                            H                                            2.088 F      CH.sub.2 C CH   CH.sub.3                                                                            H                                            ______________________________________                                    

                  TABLE 3                                                          ______________________________________                                          ##STR1094##               I                                                   No.   R.sup.1                                                                               R.sup.2 R.sup.3  R.sup.4                                                                              R.sup.5                                                                             m.p.[°C.]                      ______________________________________                                         3.001 H      H                                                                                       ##STR1095##                                                                            H     H                                          3.002 F      H                                                                                       ##STR1096##                                                                            H     H                                          3.003 H      H                                                                                       ##STR1097##                                                                            H     H                                          3.004 F      H                                                                                       ##STR1098##                                                                            H     H                                          3.005 H      H                                                                                       ##STR1099##                                                                            CH.sub.3                                                                             H                                          3.006 F      H                                                                                       ##STR1100##                                                                            CH.sub.3                                                                             H                                          3.007 H      H                                                                                       ##STR1101##                                                                            H     H                                          3.008 F      H                                                                                       ##STR1102##                                                                            H     H                                          3.009 H      H                                                                                       ##STR1103##                                                                            H     H                                          3.010 F      H                                                                                       ##STR1104##                                                                            H     H                                          3.011 H      H                                                                                       ##STR1105##                                                                            H     H    147-149                               3.012 F      H                                                                                       ##STR1106##                                                                            H     H                                          3.013 H      H                                                                                       ##STR1107##                                                                            CH.sub.3                                                                             H                                          3.014 F      H                                                                                       ##STR1108##                                                                            CH.sub.3                                                                             H                                          3.015 H      H                                                                                       ##STR1109##                                                                            H     H                                          3.016 F      H                                                                                       ##STR1110##                                                                            H     H                                          3.017 H      H                                                                                       ##STR1111##                                                                            H     H                                          3.018 F      H                                                                                       ##STR1112##                                                                            H     H                                          3.019 H      H                                                                                       ##STR1113##                                                                            H     H                                          3.020 F      H                                                                                       ##STR1114##                                                                            H     H                                          3.021 H      H                                                                                       ##STR1115##                                                                            H     H                                          3.022 F      H                                                                                       ##STR1116##                                                                            H     H                                          3.023 H      H                                                                                       ##STR1117##                                                                            H     H                                          3.024 F      H                                                                                       ##STR1118##                                                                            H     H                                          3.025 H      H                                                                                       ##STR1119##                                                                            CH.sub.3                                                                             H                                          3.026 F      H                                                                                       ##STR1120##                                                                            CH.sub.3                                                                             H                                          3.027 H      H                                                                                       ##STR1121##                                                                            H     H    188-190                               3.028 F      H                                                                                       ##STR1122##                                                                            H     H                                          3.029 H      H                                                                                       ##STR1123##                                                                            CH.sub.3                                                                             H                                          3.030 F      H                                                                                       ##STR1124##                                                                            CH.sub. 3                                                                            H                                          3.031 H      CH.sub.3                                                                                ##STR1125##                                                                            H     H                                          3.032 F      CH.sub.3                                                                                ##STR1126##                                                                            H     H                                          3.033 H      H                                                                                       ##STR1127##                                                                            H     H                                          3.034 F      H                                                                                       ##STR1128##                                                                            H     H                                          3.035 H      H                                                                                       ##STR1129##                                                                            CH.sub.3                                                                             H                                          3.036 F      H                                                                                       ##STR1130##                                                                            CH.sub.3                                                                             H                                          3.037 H      H                                                                                       ##STR1131##                                                                            H     H                                          3.038 F      H                                                                                       ##STR1132##                                                                            H     H                                          3.039 H      H                                                                                       ##STR1133##                                                                            H     H                                          3.040 F      H                                                                                       ##STR1134##                                                                            H     H                                          3.041 H      H                                                                                       ##STR1135##                                                                            CH.sub.3                                                                             H                                          3.042 F      H                                                                                       ##STR1136##                                                                            CH.sub. 3                                                                            H                                          3.043 H      H                                                                                       ##STR1137##                                                                            H     H                                          3.044 F      H                                                                                       ##STR1138##                                                                            H     H                                          3.045 H      H                                                                                       ##STR1139##                                                                            H     H                                          3.046 F      H                                                                                       ##STR1140##                                                                            H     H                                          3.047 H      H                                                                                       ##STR1141##                                                                            H     H                                          3.048 F      H                                                                                       ##STR1142##                                                                            H     H                                          3.049 H      H                                                                                       ##STR1143##                                                                            H     H                                          3.050 F      H                                                                                       ##STR1144##                                                                            H     H                                          3.051 H      H                                                                                       ##STR1145##                                                                            H     H                                          3.052 F      H                                                                                       ##STR1146##                                                                            H     H                                          3.053 H      H                                                                                       ##STR1147##                                                                            H     H                                          3.054 F      H                                                                                       ##STR1148##                                                                            H     H                                          3.055 H      H                                                                                       ##STR1149##                                                                            H     H    173-175                               3.056 F      H                                                                                       ##STR1150##                                                                            H     H                                          3.057 H      H                                                                                       ##STR1151##                                                                            H     H                                          3.058 F      H                                                                                       ##STR1152##                                                                            H     H                                          ______________________________________                                    

                  TABLE 3a                                                         ______________________________________                                          ##STR1153##               I                                                   No.   R.sup.1                                                                               A               R.sup.4                                                                             R.sup.5                                                                             m.p.[°C.]                        ______________________________________                                         3.059 H      H               H    H    237-238                                 3.060 F      H               H    H                                            3.061 H      CH.sub.3        H    H    232-234                                 3.062 F      CH.sub.3        H    H                                            3.063 H      CH.sub.2 CH.sub.3                                                                              H    H                                            3.064 F      CH.sub.2 CH.sub.3                                                                              H    H                                            3.065 H      CH(CH.sub.3).sub.2                                                                             H    H                                            3.066 F      CH(CH.sub.3).sub.2                                                                             H    H                                            3.067 H      CH.sub.2 CHCH.sub.2                                                                            H    H    168-170                                 3.068 F      CH.sub.2 CHCH.sub.2                                                                            H    H                                            3.069 H      CH.sub.2 CCH    H    H    196-198                                 3.070 F      CH.sub.2 C CH   H    H                                            3.071 H      CH.sub.2 OCH.sub.3                                                                             H    H                                            3.072 F      CH.sub.2 OCH.sub.3                                                                             H    H                                            3.073 H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                    H    H                                            3.074 F      CH.sub.2 CH.sub.2 OCH.sub.3                                                                    H    H                                            3.075 H      CH.sub.2 CO.sub.2 CH.sub.3                                                                     H    H                                            3.076 F      CH.sub.2 CO.sub.2 CH.sub.3                                                                     H    H                                            3.077 H      CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                            H    H                                            3.078 F      CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                            H    H                                            3.079 H      CH(CH.sub.3)CO.sub.2 CH.sub.3                                                                  H    H                                            3.080 F      CH(CH.sub.3)CO.sub.2 CH.sub.3                                                                  H    H                                            3.081 H      CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                         H    H                                            3.082 F      CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                         H    H                                            3.083 H      CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                         CH.sub.3                                                                            H                                            3.084 F      CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                         CH.sub.3                                                                            H                                            3.085 H      CH.sub.2 CHCH.sub.2                                                                            CH.sub.3                                                                            H                                            3.086 F      CH.sub.2 CHCH.sub.2                                                                            CH.sub.3                                                                            H                                            3.087 H      CH.sub.2 CCH    CH.sub.3                                                                            H                                            3.088 F      CH.sub.2 C CH   CH.sub.3                                                                            H                                            ______________________________________                                    

                  TABLE 4                                                          ______________________________________                                          ##STR1154##              I                                                    No.     R.sup.1  R.sup.2 R.sup.3    m.p.[°C.]                           ______________________________________                                         4.001   H        H                                                                                       ##STR1155##                                          4.002   F        H                                                                                       ##STR1156##                                          4.003   H        H                                                                                       ##STR1157##                                          4.004   F        H                                                                                       ##STR1158##                                          4.005   H        H                                                                                       ##STR1159##                                          4.006   F        H                                                                                       ##STR1160##                                          4.007   H        H                                                                                       ##STR1161##                                          4.008   F        H                                                                                       ##STR1162##                                          4.009   H        H                                                                                       ##STR1163##                                          4.010   F        H                                                                                       ##STR1164##                                          4.011   H        H                                                                                       ##STR1165##                                          4.012   F        H                                                                                       ##STR1166##                                          4.013   H        H                                                                                       ##STR1167##                                          4.014   F        H                                                                                       ##STR1168##                                          4.015   H        H                                                                                       ##STR1169##                                          4.016   H        H                                                                                       ##STR1170##                                          4.017   H        H                                                                                       ##STR1171##                                          4.018   F        H                                                                                       ##STR1172##                                          4.019   H        H                                                                                       ##STR1173##                                          4.020   F        H                                                                                       ##STR1174##                                          4.021   H        H                                                                                       ##STR1175##                                                                              150-152                                    4.022   F        H                                                                                       ##STR1176##                                          4.023   H        CH.sub.3                                                                                ##STR1177##                                          4.024   F        CH.sub.3                                                                                ##STR1178##                                          4.025   H        H                                                                                       ##STR1179##                                          4.026   F        H                                                                                       ##STR1180##                                          4.027   H        H                                                                                       ##STR1181##                                          4.028   F        H                                                                                       ##STR1182##                                          4.029   H        H                                                                                       ##STR1183##                                          4.030   F        H                                                                                       ##STR1184##                                          4.031   H        H                                                                                       ##STR1185##                                          4.032   F        H                                                                                       ##STR1186##                                          4.033   H        H                                                                                       ##STR1187##                                          4.034   F        H                                                                                       ##STR1188##                                          4.035   H        H                                                                                       ##STR1189##                                          4.036   F        H                                                                                       ##STR1190##                                          4.037   H        H                                                                                       ##STR1191##                                          4.038   F        H                                                                                       ##STR1192##                                          4.039   H        H                                                                                       ##STR1193##                                          4.040   F        H                                                                                       ##STR1194##                                          4.041   H        H                                                                                       ##STR1195##                                          4.042   F        H                                                                                       ##STR1196##                                          4.043   H        H                                                                                       ##STR1197##                                          4.044   F        H                                                                                       ##STR1198##                                          4.045   H        H                                                                                       ##STR1199##                                          4.046   F        H                                                                                       ##STR1200##                                          ______________________________________                                    

                  TABLE 4a                                                         ______________________________________                                          ##STR1201##              I                                                    No.      R.sup.1 A                m.p.[°C.]                             ______________________________________                                         4.047    H       H                140-142                                      4.048    F       H                                                             4.049    H       CH.sub.3         205-207                                      4.050    F       CH.sub.3                                                      4.051    H       CH.sub.2 CH.sub.3                                             4.052    F       CH.sub.2 CH.sub.3                                             4.053    H       CH(CH.sub.3).sub.2                                            4.054    F       CH(CH.sub.3).sub.2                                            4.055    H       CH.sub.2 CHCH.sub.2                                           4.056    F       CH.sub.2 CHCH.sub.2                                           4.057    H       CH.sub.2 CCH                                                  4.058    F       CH.sub.2 CCH                                                  4.059    H       CH.sub.2 OCH.sub.3                                            4.060    F       CH.sub.2 OCH.sub.3                                            4.061    H       CH.sub.2 CH.sub.2 OCH.sub.3                                   4.062    F       CH.sub.2 CH.sub.2 OCH.sub.3                                   4.063    H       CH.sub. 2 CO.sub.2 CH.sub.3                                   4.064    F       CH.sub.2 CO.sub.2 CH.sub.3                                    4.065    H       CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                           4.066    F       CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                           4.067    H       CH(CH.sub.3)CO.sub.2 CH.sub.3                                 4.068    F       CH(CH.sub.3)CO.sub.2 CH.sub.3                                 4.069    H       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                        4.070    F       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                        ______________________________________                                    

                  TABLE 5                                                          ______________________________________                                          ##STR1202##              I                                                    No.     R.sup.1  R.sup.2 R.sup.3    m.p.[°C.]                           ______________________________________                                         5.001   H        H                                                                                       ##STR1203##                                          5.002   F        H                                                                                       ##STR1204##                                          5.003   H        H                                                                                       ##STR1205##                                          5.004   F        H                                                                                       ##STR1206##                                          5.005   H        H                                                                                       ##STR1207##                                          5.006   F        H                                                                                       ##STR1208##                                          5.007   H        H                                                                                       ##STR1209##                                          5.008   F        H                                                                                       ##STR1210##                                          5.009   H        H                                                                                       ##STR1211##                                                                              147-151                                    5.010   F        H                                                                                       ##STR1212##                                          5.011   H        H                                                                                       ##STR1213##                                          5.012   F        H                                                                                       ##STR1214##                                          5.013   H        H                                                                                       ##STR1215##                                          5.014   F        H                                                                                       ##STR1216##                                          5.015   H        H                                                                                       ##STR1217##                                          5.016   F        H                                                                                       ##STR1218##                                          5.017   H        H                                                                                       ##STR1219##                                          5.018   F        H                                                                                       ##STR1220##                                          5.019   H        H                                                                                       ##STR1221##                                                                              133-135                                    5.020   F        H                                                                                       ##STR1222##                                          5.021   H        H                                                                                       ##STR1223##                                                                              167-169                                    5.022   F        H                                                                                       ##STR1224##                                          5.023   H        CH.sub.3                                                                                ##STR1225##                                          5.024   F        CH.sub.3                                                                                ##STR1226##                                          5.025   H        H                                                                                       ##STR1227##                                          5.026   F        H                                                                                       ##STR1228##                                          5.027   H        H                                                                                       ##STR1229##                                          5.028   F        H                                                                                       ##STR1230##                                          5.029   H        H                                                                                       ##STR1231##                                          5.030   F        H                                                                                       ##STR1232##                                          5.031   H        H                                                                                       ##STR1233##                                          5.032   F        H                                                                                       ##STR1234##                                          5.033   H        H                                                                                       ##STR1235##                                          5.034   F        H                                                                                       ##STR1236##                                          5.035   H        H                                                                                       ##STR1237##                                          5.036   F        H                                                                                       ##STR1238##                                          5.037   H        H                                                                                       ##STR1239##                                          5.038   F        H                                                                                       ##STR1240##                                          5.039   H        H                                                                                       ##STR1241##                                          5.040   F        H                                                                                       ##STR1242##                                          5.041   H        H                                                                                       ##STR1243##                                                                              206-207                                    5.042   F        H                                                                                       ##STR1244##                                          5.043   H        H                                                                                       ##STR1245##                                          5.044   F        H                                                                                       ##STR1246##                                          5.045   H        H                                                                                       ##STR1247##                                          5.046   F        H                                                                                       ##STR1248##                                          ______________________________________                                    

                  TABLE 6                                                          ______________________________________                                          ##STR1249##              I                                                    No.     R.sup.1  R.sup.2 R.sup.3    m.p.[°C.]                           ______________________________________                                         6.001   H        H                                                                                       ##STR1250##                                          6.002   F        H                                                                                       ##STR1251##                                          6.003   H        H                                                                                       ##STR1252##                                          6.004   F        H                                                                                       ##STR1253##                                          6.005   H        H                                                                                       ##STR1254##                                          6.006   F        H                                                                                       ##STR1255##                                          6.007   H        H                                                                                       ##STR1256##                                          6.008   F        H                                                                                       ##STR1257##                                          6.009   H        H                                                                                       ##STR1258##                                          6.010   F        H                                                                                       ##STR1259##                                          6.011   H        H                                                                                       ##STR1260##                                          6.012   F        H                                                                                       ##STR1261##                                          6.013   H        H                                                                                       ##STR1262##                                          6.014   F        H                                                                                       ##STR1263##                                          6.015   H        H                                                                                       ##STR1264##                                          6.016   F        H                                                                                       ##STR1265##                                          6.017   H        H                                                                                       ##STR1266##                                          6.018   F        H                                                                                       ##STR1267##                                          6.019   H        H                                                                                       ##STR1268##                                          6.020   F        H                                                                                       ##STR1269##                                          6.021   H        H                                                                                       ##STR1270##                                          6.022   F        H                                                                                       ##STR1271##                                          6.023   H        CH.sub.3                                                                                ##STR1272##                                          6.024   F        CH.sub.3                                                                                ##STR1273##                                          6.025   H        H                                                                                       ##STR1274##                                          6.026   F        H                                                                                       ##STR1275##                                          6.027   H        H                                                                                       ##STR1276##                                          6.028   F        H                                                                                       ##STR1277##                                          6.029   H        H                                                                                       ##STR1278##                                          6.030   F        H                                                                                       ##STR1279##                                                                              187-189                                    6.031   H        H                                                                                       ##STR1280##                                          6.032   F        H                                                                                       ##STR1281##                                          6.033   H        H                                                                                       ##STR1282##                                          6.034   F        H                                                                                       ##STR1283##                                          6.035   H        H                                                                                       ##STR1284##                                          6.036   F        H                                                                                       ##STR1285##                                          6.037   H        H                                                                                       ##STR1286##                                          6.038   F        H                                                                                       ##STR1287##                                          6.039   H        H                                                                                       ##STR1288##                                          6.040   F        H                                                                                       ##STR1289##                                          6.041   H        H                                                                                       ##STR1290##                                          6.042   F        H                                                                                       ##STR1291##                                          6.043   H        H                                                                                       ##STR1292##                                          6.044   F        H                                                                                       ##STR1293##                                          6.045   H        H                                                                                       ##STR1294##                                          6.046   F        H                                                                                       ##STR1295##                                          ______________________________________                                    

USE EXAMPLES

The action of the N-aryltetrahydrophthalimide compounds of the formula I on plant growth is demonstrated by the following greenhouse experiments:

The vessels employed were plastic flowerpots having a volume of 300 cm³ and filled with a sandy loam containing about 3.0% humus. The seeds of the test plants were sown separately, according to species.

For the postemergence treatment, either plants which had been sown in the pots and grown there were selected, or they were cultivated separately as seedlings and transplanted to the pots a few days before being treated.

Depending on growth form, the plants were grown to a height of from 3 to 15 cm before being treated with the active ingredients which were suspended or emulsified in water and sprayed through finely distributing nozzles. The application rates for postemergence treatment were 0.06 and 0.125 kg of active ingredient per hectare.

The pots were set up in the greenhouse, species from warmer climates in warmer areas (20° to 35° C.) and species from moderate climates at 10 to 20° C. The experiments were run for from 2 to 4 weeks. During this time the plants were tended and their reactions to the various treatments assessed.

The assessment scale was 0 to 100, 100 denoting nonemergence or complete destruction of at least the visible plant parts, and 0 denoting no damage or normal growth.

The plants used in the greenhouse experiments were: Amaranthus retroflexus, Galium aparine, Stellaria media, Veronica spp., Oryza sativa, Solanum higrum, and Triticum aestivum.

The compounds 1.027 and 1.029, applied postemergence at rates of 0.06 and 0.125 kg/ha, gave excellent control of unwanted broadleaved plants, and were well tolerated by rice and wheat. Compound 3.067, applied postemergence at a rate of 0.06 kg/ha, combated unwanted broadleaved plants without causing any appreciable damage to rice. 

We claim:
 1. An N-aryltetrahydrophthalimide compound of the formula I ##STR1296## where the substituents and indices have the following meanings: n is 0 or 1, R¹ is hydrogen or halogen, Y is --O-- or --S--, R² is hydrogen or C₁ -C₃ -alkyl, and R³ is phenyl which is unsubstituted or monosubstituted to trisubstituted by C₁ - or C₂ -alkyl, halogen, methoxy, nitro, and/or cyano.
 2. A herbicide containing a herbicidally effective amount of an N-aryltetrahydrophthalimide compound of the formula I as defined in claim 1 and inert additives.
 3. A herbicide containing a herbicidally effective amount of an N-aryltetrahydrophthalimide compound of the formula I as defined in claim 1 and further active constituents.
 4. A method for controlling undesirable plant growth, wherein the undesirable plants, their habitat or both the undesirable plants and their habitat, are treated with a herbicidally effective amount of an N-aryltetrahydrophthalimide compound of the formula I, as defined in claim
 1. 5. An N-aryltetrahydrophthalimide compound of the formula I ##STR1297## where the substituents and indices have the following meanings: n is 0 or 1, R¹ is hydrogen or halogen, Y is --O-- or --S--, R² is hydrogen or C₁ -C₃ -alkyl, and R³ is 2-tetrahydrothiopyranyl, 3-tetrahydrothiopyranyl, 4-tetrahydrothiopyranyl, 5,6-dihydro-2H-thiopyranyl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl or 5,6-dihydro-2H-pyranyl each of which may be monosubstituted to trisubstituted by C₁ -C₃ -alkyl.
 6. A herbicide containing a herbicidally effective amount of an N-aryltetrahydrophthalimide compound of the formula I as defined in claim 5 and inert additives.
 7. A herbicide containing a herbicidally effective amount of an N-aryltetrahydrophthalimide compound of the formula I as defined in claim 5 and further active constituents.
 8. A method for controlling undesirable plant growth, wherein the undesirable plants, their habitat or both the undesirable plants and their habitat, are treated with a herbicidally effective amount of an N-aryltetrahydrophthalimide compound of the formula I, as defined in claim
 5. 9. An N-aryltetrahydrophthalimide compound of the formula I ##STR1298## where the substituents and indices have the following meanings: n is 0 or 1, R¹ is hydrogen or halogen, Y is --O-- or --S--, R² is hydrogen or C₁ -C₃ -alkyl, and R³ is 2-tetrahydrofuryl, 3-tetrahydrofuryl, 2-tetrahydrothienyl or 3-tetrahydrothienyl each of which may be monosubstituted to trisubstituted by C₁ -C₃ -alkyl.
 10. A herbicide containing a herbicidally effective amount of an N-aryltetrahydrophthalimide compound of the formula I as defined in claim 9 and inert additives.
 11. A herbicide containing a herbicidally effective amount of a N-aryltetrahydrophthalimide compound of the formula I as defined in claim 9 and further active constituents.
 12. A method for controlling undesirable plant growth, wherein the undesirable plants, their habitat or both the undesirable plants and their habitat, are treated with a herbicidally effective amount of an N-aryltetrahydrophthalimide compound of the formula I, as defined in claim
 9. 